The quality is guaranteed. If you find the product is wrong compared with COA, we promise 100% refund or change product. COA and HPLC will be shipped out with goods. You can also inform your analysis method and we will follow your analysis method
Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities
Cas:4368-28-9
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inquiry1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s
Cas:4368-28-9
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inquiryTETRODOTOXIN CAS: 4368-28-9 Molecular Formula: C11H17N3O8 Home Product Category 4368-28-9 4368-28-9 - Names and Identifiers Name TETRODOTOXIN Synonyms TETRODOTOXIN PUFFERFISHTOXIN PUFFERFISHPOISONING Tetrodo
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inquiryOur main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block
With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin
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inquiry1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized
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inquiryBeluga chemical professional supply Tetrodotoxin CAS 4368-28-9 Why choose Beluga chemical 1. Beluga Chemical has a professional RESEARCH and development team and strong technical force to ensure technical support and research capabilities. 2. M
Cas:4368-28-9
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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inquirySpecification:USP/EP Month production ablity:50kg/Month Low price& High quality Manufacturer Appearance:white powder Storage:Room Temperature Package:in aluminum bag and foil bag or as customers' require Application:4368-28-9 Transportati
Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
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inquiryLorcaserin(856681-05-5)is an orally administered agent and a selective 5-HT2C receptor agonist for the treatment of obesity. It had been approved for marketing in US by FDA on 27 June in 2012. In clinical studies, lorcaserin h
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inquiryChengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medic
J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia
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inquiryWhy Choose Us: 1. Factory direct sales, so we can provide the competitive price and high quality product base on 8 years of production and R&D experience. 2. It is available in stock for quick shipment.Products could be packaged according to cu
Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi
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inquiryfavourable price of Tetrodotoxin 4368-28-9 top quality supplierAppearance:powde Storage:Store in cool and dry place. Package:according to customers' requirements Application:Multipurpose intermediate Transportation:By air(EMS or EUB or FedEx or TN
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inquirySuperior quality, moderate price & quick delivery. Appearance:white powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:25kg/drum, or as per your request. Application:Used as Pharmaceutical Intermediates Tr
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inquiryWe can offer products of different specifications Appearance:bottle Storage:-20℃ Application:Determination of corresponding toxins
Our Advantages A. International Top level TechnologyOur company owned biomedicine experts are famous at home and abroad with rich experience in research and development in the field of efficient chiral functional molecules research and development an
factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B
Cas:4368-28-9
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inquiryProduct Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,
Hangzhou Huarong Pharm Co., Ltd.established since 2006 , has been actively developing specialty products for Finished Dosages, APIs, Intermediates, and Fine chemicals markets in North America, Europe, Korea, Japan, Mid-East and all over the World. Hu
Zhenyu biotech exported this product to many countries and regions at best price. if you are looking for the material's manufacturer or supplier in china, zhenyu biotech is your best choice. pls contact with us freely for getting detailed
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inquiryHangzhou Fanda Chemical Co.,Ltd (FandaChem) , a China-based chemical company, specialize in exporting Tetrodotoxin;TTX CAS:4368-28-9, Please contact us by email freely. We are leading exporter in China. If you really need this cargo,
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inquiryShandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W
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inquiry1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer
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Min.Order:1 Metric Ton
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Type:Trading Company
inquiryGOLDEN PHARMA CO.,LIMITED.is a professional pharmaceutical company,our team have more than 20years expereince in pharmaceutical production and sales. we are a professional technical enterprise specializing in the R & D, production,QA regulation
We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp
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inquiry1, High quality with competitive price:2, Fast and safe delivery3.Excellent pre-sales and after-sales service4. Well-trained and professional technologist and sales with rich experience in the field for 5-10 yearsAppearance:see detailed specification
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inquirytetradotoxin
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3h; | 96.4% |
Conditions | Yield |
---|---|
In water-d2; trifluoroacetic acid for 96h; | A 66% B 15% |
tetradotoxin
Conditions | Yield |
---|---|
In water-d2; trifluoroacetic acid for 96h; | 63% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In water at 20℃; | A 58% B 36% |
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HgCl2; Et3N / dimethylformamide / 20 °C 2: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
Acetic acid (1R,3S,5S,6S,7S,8R,9S,10S)-9-acetoxy-9-acetoxymethyl-8-dimethoxymethyl-3,10-dihydroxy-7-(2,2,2-trichloro-acetylamino)-2,4-dioxa-tricyclo[3.3.1.13,7]dec-6-yl ester
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 2,6-lutidine / CH2Cl2 / 0 °C 2: diisobutylaluminum hydride / CH2Cl2 / -40 °C 3: HgCl2; Et3N / dimethylformamide / 20 °C 4: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
2,2,2-Trichloro-N-[(1R,2S,5R,6S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-5,6-bis-triethylsilanyloxy-1-vinyl-cyclohex-3-enyl]-acetamide
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 16 steps 1.1: selenium dioxide; pyridine N-oxide / dioxane / Heating 1.2: 48 percent / NaBH4; CeCl3*7H2O / methanol / 0 °C 2.1: 2,6-lutidine / CH2Cl2 / 0 °C 2.2: 83 percent / m-chloroperbenzoic acid; Na2HPO4 / CH2Cl2 / 20 °C 3.1: 90 percent / O3; Et3N / CH2Cl2 / -78 °C 4.1: 70 percent / EtMgBr / tetrahydrofuran / 0 °C 5.1: 4-dimethylaminopyridine / pyridine / 20 °C 5.2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / -10 °C 6.1: KMnO4; NaIO4; NaHCO3 / 2-methyl-propan-2-ol; H2O / 50 °C 7.1: H2O2; NaHCO3 / methanol / 20 °C 8.1: 2,6-lutidine / CH2Cl2 / -40 °C 9.1: pyridine / 20 °C 10.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 10.2: 71 percent / pyridine / 20 °C 11.1: periodic acid / methyl acetate / 20 °C 11.2: camphor sulfonic acid / methanol / 20 °C 12.1: aq. NH3 / methanol / 0 °C 13.1: 2,6-lutidine / CH2Cl2 / 0 °C 14.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 15.1: HgCl2; Et3N / dimethylformamide / 20 °C 16.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
C25H36Cl3NO12Si
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 2: HgCl2; Et3N / dimethylformamide / 20 °C 3: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
Acetic acid (1R,3S,5S,6S,7R,8R,9S,10S)-3,6,9-triacetoxy-9-acetoxymethyl-8-dimethoxymethyl-7-(2,2,2-trichloro-acetylamino)-2,4-dioxa-tricyclo[3.3.1.13,7]dec-10-yl ester
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aq. NH3 / methanol / 0 °C 2: 2,6-lutidine / CH2Cl2 / 0 °C 3: diisobutylaluminum hydride / CH2Cl2 / -40 °C 4: HgCl2; Et3N / dimethylformamide / 20 °C 5: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
2,2,2-Trichloro-N-[(1R,2S,5R,6S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxymethyl-5,6-bis-triethylsilanyloxy-1-vinyl-cyclohex-3-enyl]-acetamide
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1.1: 2,6-lutidine / CH2Cl2 / 0 °C 1.2: 83 percent / m-chloroperbenzoic acid; Na2HPO4 / CH2Cl2 / 20 °C 2.1: 90 percent / O3; Et3N / CH2Cl2 / -78 °C 3.1: 70 percent / EtMgBr / tetrahydrofuran / 0 °C 4.1: 4-dimethylaminopyridine / pyridine / 20 °C 4.2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / -10 °C 5.1: KMnO4; NaIO4; NaHCO3 / 2-methyl-propan-2-ol; H2O / 50 °C 6.1: H2O2; NaHCO3 / methanol / 20 °C 7.1: 2,6-lutidine / CH2Cl2 / -40 °C 8.1: pyridine / 20 °C 9.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 9.2: 71 percent / pyridine / 20 °C 10.1: periodic acid / methyl acetate / 20 °C 10.2: camphor sulfonic acid / methanol / 20 °C 11.1: aq. NH3 / methanol / 0 °C 12.1: 2,6-lutidine / CH2Cl2 / 0 °C 13.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 14.1: HgCl2; Et3N / dimethylformamide / 20 °C 15.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
Acetic acid (1R,3S,5S,6S,7R,8S,9S,10S)-3,6,9-triacetoxy-9-acetoxymethyl-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-(2,2,2-trichloro-acetylamino)-2,4-dioxa-tricyclo[3.3.1.13,7]dec-10-yl ester
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: periodic acid / methyl acetate / 20 °C 1.2: camphor sulfonic acid / methanol / 20 °C 2.1: aq. NH3 / methanol / 0 °C 3.1: 2,6-lutidine / CH2Cl2 / 0 °C 4.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 5.1: HgCl2; Et3N / dimethylformamide / 20 °C 6.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 2,6-lutidine / CH2Cl2 / -40 °C 2.1: pyridine / 20 °C 3.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 3.2: 71 percent / pyridine / 20 °C 4.1: periodic acid / methyl acetate / 20 °C 4.2: camphor sulfonic acid / methanol / 20 °C 5.1: aq. NH3 / methanol / 0 °C 6.1: 2,6-lutidine / CH2Cl2 / 0 °C 7.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 8.1: HgCl2; Et3N / dimethylformamide / 20 °C 9.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
2,2,2-Trichloro-N-[(1S,2S,3R,4S,5S,6S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-formyl-4,5-bis-triethylsilanyloxy-6-triethylsilanyloxymethyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-acetamide
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1.1: 70 percent / EtMgBr / tetrahydrofuran / 0 °C 2.1: 4-dimethylaminopyridine / pyridine / 20 °C 2.2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / -10 °C 3.1: KMnO4; NaIO4; NaHCO3 / 2-methyl-propan-2-ol; H2O / 50 °C 4.1: H2O2; NaHCO3 / methanol / 20 °C 5.1: 2,6-lutidine / CH2Cl2 / -40 °C 6.1: pyridine / 20 °C 7.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 7.2: 71 percent / pyridine / 20 °C 8.1: periodic acid / methyl acetate / 20 °C 8.2: camphor sulfonic acid / methanol / 20 °C 9.1: aq. NH3 / methanol / 0 °C 10.1: 2,6-lutidine / CH2Cl2 / 0 °C 11.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 12.1: HgCl2; Et3N / dimethylformamide / 20 °C 13.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
2,2,2-Trichloro-N-[(1S,2S,3R,4S,5S,6S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,5-bis-triethylsilanyloxy-6-triethylsilanyloxymethyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-acetamide
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1.1: 90 percent / O3; Et3N / CH2Cl2 / -78 °C 2.1: 70 percent / EtMgBr / tetrahydrofuran / 0 °C 3.1: 4-dimethylaminopyridine / pyridine / 20 °C 3.2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / -10 °C 4.1: KMnO4; NaIO4; NaHCO3 / 2-methyl-propan-2-ol; H2O / 50 °C 5.1: H2O2; NaHCO3 / methanol / 20 °C 6.1: 2,6-lutidine / CH2Cl2 / -40 °C 7.1: pyridine / 20 °C 8.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 8.2: 71 percent / pyridine / 20 °C 9.1: periodic acid / methyl acetate / 20 °C 9.2: camphor sulfonic acid / methanol / 20 °C 10.1: aq. NH3 / methanol / 0 °C 11.1: 2,6-lutidine / CH2Cl2 / 0 °C 12.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 13.1: HgCl2; Et3N / dimethylformamide / 20 °C 14.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
Acetic acid (R)-1-[(1S,2S,3S,4S,5S,6S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(2,2,2-trichloro-acetylamino)-4,5-bis-triethylsilanyloxy-6-triethylsilanyloxymethyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-prop-2-ynyl ester
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: KMnO4; NaIO4; NaHCO3 / 2-methyl-propan-2-ol; H2O / 50 °C 2.1: H2O2; NaHCO3 / methanol / 20 °C 3.1: 2,6-lutidine / CH2Cl2 / -40 °C 4.1: pyridine / 20 °C 5.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 5.2: 71 percent / pyridine / 20 °C 6.1: periodic acid / methyl acetate / 20 °C 6.2: camphor sulfonic acid / methanol / 20 °C 7.1: aq. NH3 / methanol / 0 °C 8.1: 2,6-lutidine / CH2Cl2 / 0 °C 9.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 10.1: HgCl2; Et3N / dimethylformamide / 20 °C 11.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
2,2,2-Trichloro-N-[(1R,4S,5S,6S,7S,8S,9S)-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dihydroxy-3-oxo-6,7-bis-triethylsilanyloxy-8-triethylsilanyloxymethyl-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: pyridine / 20 °C 2.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 2.2: 71 percent / pyridine / 20 °C 3.1: periodic acid / methyl acetate / 20 °C 3.2: camphor sulfonic acid / methanol / 20 °C 4.1: aq. NH3 / methanol / 0 °C 5.1: 2,6-lutidine / CH2Cl2 / 0 °C 6.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 7.1: HgCl2; Et3N / dimethylformamide / 20 °C 8.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
Acetic acid (1R,4S,5S,6S,7S,8S,9S)-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-3-oxo-5-(2,2,2-trichloro-acetylamino)-6,7-bis-triethylsilanyloxy-8-triethylsilanyloxymethyl-2-oxa-bicyclo[3.3.1]non-4-yl ester
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 1.2: 71 percent / pyridine / 20 °C 2.1: periodic acid / methyl acetate / 20 °C 2.2: camphor sulfonic acid / methanol / 20 °C 3.1: aq. NH3 / methanol / 0 °C 4.1: 2,6-lutidine / CH2Cl2 / 0 °C 5.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 6.1: HgCl2; Et3N / dimethylformamide / 20 °C 7.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
2,2,2-Trichloro-N-[(1S,2S,3S,4S,5S,6S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-((R)-1-hydroxy-3-trimethylsilanyl-prop-2-ynyl)-4,5-bis-triethylsilanyloxy-6-triethylsilanyloxymethyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-acetamide
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: 4-dimethylaminopyridine / pyridine / 20 °C 1.2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / -10 °C 2.1: KMnO4; NaIO4; NaHCO3 / 2-methyl-propan-2-ol; H2O / 50 °C 3.1: H2O2; NaHCO3 / methanol / 20 °C 4.1: 2,6-lutidine / CH2Cl2 / -40 °C 5.1: pyridine / 20 °C 6.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 6.2: 71 percent / pyridine / 20 °C 7.1: periodic acid / methyl acetate / 20 °C 7.2: camphor sulfonic acid / methanol / 20 °C 8.1: aq. NH3 / methanol / 0 °C 9.1: 2,6-lutidine / CH2Cl2 / 0 °C 10.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 11.1: HgCl2; Et3N / dimethylformamide / 20 °C 12.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
(S)-3-Acetoxy-3-[(1S,2S,3S,4S,5S,6S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(2,2,2-trichloro-acetylamino)-4,5-bis-triethylsilanyloxy-6-triethylsilanyloxymethyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2-oxo-propionic acid
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: H2O2; NaHCO3 / methanol / 20 °C 2.1: 2,6-lutidine / CH2Cl2 / -40 °C 3.1: pyridine / 20 °C 4.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 4.2: 71 percent / pyridine / 20 °C 5.1: periodic acid / methyl acetate / 20 °C 5.2: camphor sulfonic acid / methanol / 20 °C 6.1: aq. NH3 / methanol / 0 °C 7.1: 2,6-lutidine / CH2Cl2 / 0 °C 8.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 9.1: HgCl2; Et3N / dimethylformamide / 20 °C 10.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
2,2,2-Trichloro-N-[(1R,2S,5R,6S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,6-dihydroxy-4-methyl-1-vinyl-cyclohex-3-enyl]-acetamide
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 17 steps 1.1: 86 percent / pyridine / acetonitrile / 20 °C 2.1: selenium dioxide; pyridine N-oxide / dioxane / Heating 2.2: 48 percent / NaBH4; CeCl3*7H2O / methanol / 0 °C 3.1: 2,6-lutidine / CH2Cl2 / 0 °C 3.2: 83 percent / m-chloroperbenzoic acid; Na2HPO4 / CH2Cl2 / 20 °C 4.1: 90 percent / O3; Et3N / CH2Cl2 / -78 °C 5.1: 70 percent / EtMgBr / tetrahydrofuran / 0 °C 6.1: 4-dimethylaminopyridine / pyridine / 20 °C 6.2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / -10 °C 7.1: KMnO4; NaIO4; NaHCO3 / 2-methyl-propan-2-ol; H2O / 50 °C 8.1: H2O2; NaHCO3 / methanol / 20 °C 9.1: 2,6-lutidine / CH2Cl2 / -40 °C 10.1: pyridine / 20 °C 11.1: tetrabutylammonium fluoride / acetonitrile / 0 °C 11.2: 71 percent / pyridine / 20 °C 12.1: periodic acid / methyl acetate / 20 °C 12.2: camphor sulfonic acid / methanol / 20 °C 13.1: aq. NH3 / methanol / 0 °C 14.1: 2,6-lutidine / CH2Cl2 / 0 °C 15.1: diisobutylaluminum hydride / CH2Cl2 / -40 °C 16.1: HgCl2; Et3N / dimethylformamide / 20 °C 17.1: 36 percent / trifluoroacetic acid / H2O / 20 °C View Scheme |
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 15 percent / trifluoroacetic acid; D2O / 96 h 2: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetaldehyde
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 34 steps 1.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 2.1: 1.60 g / benzene; methanol / 1 h / 20 °C 3.1: CH2Cl2 / 0.25 h / 0 °C 4.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 5.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 6.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 7.1: pyridine / 10 h / 50 °C 8.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 9.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 10.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 11.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 12.1: Ac2O; DMSO / 2 h / 20 °C 13.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 14.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 15.1: 89 percent / TFA / methanol / 3 h / 20 °C 16.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 17.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 18.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 19.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 20.1: NaBH4 / methanol / 0.25 h / -78 °C 21.1: Et3N; MeOH / 28.8 h / 15 °C 22.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 22.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 23.1: Pd(OH)2/C / methanol / 12 h / 20 °C 24.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 25.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 26.1: CAN / acetonitrile; H2O / 2 h / 85 °C 27.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 28.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 29.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 30.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 31.1: HCl; dioxane / 24 h 32.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 33.1: 18 percent / Et3N / aq. methanol / 8 h / 20 °C 34.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 35 steps 1.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 2.1: 1.60 g / benzene; methanol / 1 h / 20 °C 3.1: CH2Cl2 / 0.25 h / 0 °C 4.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 5.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 6.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 7.1: pyridine / 10 h / 50 °C 8.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 9.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 10.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 11.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 12.1: Ac2O; DMSO / 2 h / 20 °C 13.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 14.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 15.1: 89 percent / TFA / methanol / 3 h / 20 °C 16.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 17.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 18.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 19.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 20.1: NaBH4 / methanol / 0.25 h / -78 °C 21.1: Et3N; MeOH / 28.8 h / 15 °C 22.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 22.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 23.1: Pd(OH)2/C / methanol / 12 h / 20 °C 24.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 25.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 26.1: CAN / acetonitrile; H2O / 2 h / 85 °C 27.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 28.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 29.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 30.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 31.1: HCl; dioxane / 24 h 32.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 33.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 34.1: 15 percent / trifluoroacetic acid; D2O / 96 h 35.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 34 steps 1.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 2.1: 1.60 g / benzene; methanol / 1 h / 20 °C 3.1: CH2Cl2 / 0.25 h / 0 °C 4.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 5.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 6.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 7.1: pyridine / 10 h / 50 °C 8.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 9.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 10.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 11.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 12.1: Ac2O; DMSO / 2 h / 20 °C 13.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 14.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 15.1: 89 percent / TFA / methanol / 3 h / 20 °C 16.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 17.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 18.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 19.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 20.1: NaBH4 / methanol / 0.25 h / -78 °C 21.1: Et3N; MeOH / 28.8 h / 15 °C 22.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 22.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 23.1: Pd(OH)2/C / methanol / 12 h / 20 °C 24.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 25.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 26.1: CAN / acetonitrile; H2O / 2 h / 85 °C 27.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 28.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 29.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 30.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 31.1: HCl; dioxane / 24 h 32.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 33.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 34.1: 66 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
(1S,4R,6R)-4-Benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-hydroxy-eth-(E)-ylidene]-cyclohex-2-enol
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 35 steps 1.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 2.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 3.1: 1.60 g / benzene; methanol / 1 h / 20 °C 4.1: CH2Cl2 / 0.25 h / 0 °C 5.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 6.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 7.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 8.1: pyridine / 10 h / 50 °C 9.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 10.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 11.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 12.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 13.1: Ac2O; DMSO / 2 h / 20 °C 14.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 15.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 16.1: 89 percent / TFA / methanol / 3 h / 20 °C 17.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 18.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 19.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 20.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 21.1: NaBH4 / methanol / 0.25 h / -78 °C 22.1: Et3N; MeOH / 28.8 h / 15 °C 23.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 23.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 24.1: Pd(OH)2/C / methanol / 12 h / 20 °C 25.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 26.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 27.1: CAN / acetonitrile; H2O / 2 h / 85 °C 28.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 29.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 30.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 31.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 32.1: HCl; dioxane / 24 h 33.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 34.1: 18 percent / Et3N / aq. methanol / 8 h / 20 °C 35.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 36 steps 1.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 2.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 3.1: 1.60 g / benzene; methanol / 1 h / 20 °C 4.1: CH2Cl2 / 0.25 h / 0 °C 5.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 6.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 7.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 8.1: pyridine / 10 h / 50 °C 9.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 10.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 11.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 12.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 13.1: Ac2O; DMSO / 2 h / 20 °C 14.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 15.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 16.1: 89 percent / TFA / methanol / 3 h / 20 °C 17.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 18.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 19.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 20.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 21.1: NaBH4 / methanol / 0.25 h / -78 °C 22.1: Et3N; MeOH / 28.8 h / 15 °C 23.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 23.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 24.1: Pd(OH)2/C / methanol / 12 h / 20 °C 25.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 26.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 27.1: CAN / acetonitrile; H2O / 2 h / 85 °C 28.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 29.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 30.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 31.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 32.1: HCl; dioxane / 24 h 33.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 34.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 35.1: 15 percent / trifluoroacetic acid; D2O / 96 h 36.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 35 steps 1.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 2.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 3.1: 1.60 g / benzene; methanol / 1 h / 20 °C 4.1: CH2Cl2 / 0.25 h / 0 °C 5.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 6.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 7.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 8.1: pyridine / 10 h / 50 °C 9.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 10.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 11.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 12.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 13.1: Ac2O; DMSO / 2 h / 20 °C 14.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 15.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 16.1: 89 percent / TFA / methanol / 3 h / 20 °C 17.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 18.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 19.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 20.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 21.1: NaBH4 / methanol / 0.25 h / -78 °C 22.1: Et3N; MeOH / 28.8 h / 15 °C 23.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 23.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 24.1: Pd(OH)2/C / methanol / 12 h / 20 °C 25.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 26.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 27.1: CAN / acetonitrile; H2O / 2 h / 85 °C 28.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 29.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 30.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 31.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 32.1: HCl; dioxane / 24 h 33.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 34.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 35.1: 66 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetic acid methyl ester
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 32 steps 1.1: CH2Cl2 / 0.25 h / 0 °C 2.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 3.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 4.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 5.1: pyridine / 10 h / 50 °C 6.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 7.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 8.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 9.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 10.1: Ac2O; DMSO / 2 h / 20 °C 11.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 12.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 13.1: 89 percent / TFA / methanol / 3 h / 20 °C 14.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 15.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 16.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 17.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 18.1: NaBH4 / methanol / 0.25 h / -78 °C 19.1: Et3N; MeOH / 28.8 h / 15 °C 20.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 20.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 21.1: Pd(OH)2/C / methanol / 12 h / 20 °C 22.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 23.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 24.1: CAN / acetonitrile; H2O / 2 h / 85 °C 25.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 26.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 27.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 28.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 29.1: HCl; dioxane / 24 h 30.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 31.1: 18 percent / Et3N / aq. methanol / 8 h / 20 °C 32.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 33 steps 1.1: CH2Cl2 / 0.25 h / 0 °C 2.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 3.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 4.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 5.1: pyridine / 10 h / 50 °C 6.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 7.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 8.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 9.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 10.1: Ac2O; DMSO / 2 h / 20 °C 11.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 12.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 13.1: 89 percent / TFA / methanol / 3 h / 20 °C 14.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 15.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 16.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 17.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 18.1: NaBH4 / methanol / 0.25 h / -78 °C 19.1: Et3N; MeOH / 28.8 h / 15 °C 20.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 20.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 21.1: Pd(OH)2/C / methanol / 12 h / 20 °C 22.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 23.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 24.1: CAN / acetonitrile; H2O / 2 h / 85 °C 25.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 26.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 27.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 28.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 29.1: HCl; dioxane / 24 h 30.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 31.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 32.1: 15 percent / trifluoroacetic acid; D2O / 96 h 33.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 32 steps 1.1: CH2Cl2 / 0.25 h / 0 °C 2.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 3.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 4.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 5.1: pyridine / 10 h / 50 °C 6.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 7.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 8.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 9.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 10.1: Ac2O; DMSO / 2 h / 20 °C 11.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 12.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 13.1: 89 percent / TFA / methanol / 3 h / 20 °C 14.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 15.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 16.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 17.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 18.1: NaBH4 / methanol / 0.25 h / -78 °C 19.1: Et3N; MeOH / 28.8 h / 15 °C 20.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 20.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 21.1: Pd(OH)2/C / methanol / 12 h / 20 °C 22.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 23.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 24.1: CAN / acetonitrile; H2O / 2 h / 85 °C 25.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 26.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 27.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 28.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 29.1: HCl; dioxane / 24 h 30.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 31.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 32.1: 66 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 33 steps 1.1: 1.60 g / benzene; methanol / 1 h / 20 °C 2.1: CH2Cl2 / 0.25 h / 0 °C 3.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 4.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 5.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 6.1: pyridine / 10 h / 50 °C 7.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 8.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 9.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 10.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 11.1: Ac2O; DMSO / 2 h / 20 °C 12.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 13.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 14.1: 89 percent / TFA / methanol / 3 h / 20 °C 15.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 16.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 17.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 18.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 19.1: NaBH4 / methanol / 0.25 h / -78 °C 20.1: Et3N; MeOH / 28.8 h / 15 °C 21.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 21.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 22.1: Pd(OH)2/C / methanol / 12 h / 20 °C 23.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 24.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 25.1: CAN / acetonitrile; H2O / 2 h / 85 °C 26.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 27.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 28.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 29.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 30.1: HCl; dioxane / 24 h 31.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 32.1: 18 percent / Et3N / aq. methanol / 8 h / 20 °C 33.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 34 steps 1.1: 1.60 g / benzene; methanol / 1 h / 20 °C 2.1: CH2Cl2 / 0.25 h / 0 °C 3.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 4.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 5.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 6.1: pyridine / 10 h / 50 °C 7.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 8.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 9.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 10.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 11.1: Ac2O; DMSO / 2 h / 20 °C 12.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 13.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 14.1: 89 percent / TFA / methanol / 3 h / 20 °C 15.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 16.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 17.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 18.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 19.1: NaBH4 / methanol / 0.25 h / -78 °C 20.1: Et3N; MeOH / 28.8 h / 15 °C 21.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 21.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 22.1: Pd(OH)2/C / methanol / 12 h / 20 °C 23.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 24.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 25.1: CAN / acetonitrile; H2O / 2 h / 85 °C 26.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 27.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 28.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 29.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 30.1: HCl; dioxane / 24 h 31.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 32.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 33.1: 15 percent / trifluoroacetic acid; D2O / 96 h 34.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 33 steps 1.1: 1.60 g / benzene; methanol / 1 h / 20 °C 2.1: CH2Cl2 / 0.25 h / 0 °C 3.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 4.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 5.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 6.1: pyridine / 10 h / 50 °C 7.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 8.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 9.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 10.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 11.1: Ac2O; DMSO / 2 h / 20 °C 12.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 13.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 14.1: 89 percent / TFA / methanol / 3 h / 20 °C 15.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 16.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 17.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 18.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 19.1: NaBH4 / methanol / 0.25 h / -78 °C 20.1: Et3N; MeOH / 28.8 h / 15 °C 21.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 21.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 22.1: Pd(OH)2/C / methanol / 12 h / 20 °C 23.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 24.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 25.1: CAN / acetonitrile; H2O / 2 h / 85 °C 26.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 27.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 28.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 29.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 30.1: HCl; dioxane / 24 h 31.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 32.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 33.1: 66 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
Benzoic acid (1S,2R,3S,4R,5S,6R)-2-acetoxy-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-(2-oxo-ethyl)-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 18 steps 1.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 2.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 3.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 4.1: NaBH4 / methanol / 0.25 h / -78 °C 5.1: Et3N; MeOH / 28.8 h / 15 °C 6.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 6.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 7.1: Pd(OH)2/C / methanol / 12 h / 20 °C 8.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 9.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 10.1: CAN / acetonitrile; H2O / 2 h / 85 °C 11.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 12.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 13.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 14.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 15.1: HCl; dioxane / 24 h 16.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 17.1: 18 percent / Et3N / aq. methanol / 8 h / 20 °C 18.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 19 steps 1.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 2.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 3.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 4.1: NaBH4 / methanol / 0.25 h / -78 °C 5.1: Et3N; MeOH / 28.8 h / 15 °C 6.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 6.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 7.1: Pd(OH)2/C / methanol / 12 h / 20 °C 8.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 9.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 10.1: CAN / acetonitrile; H2O / 2 h / 85 °C 11.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 12.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 13.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 14.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 15.1: HCl; dioxane / 24 h 16.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 17.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 18.1: 15 percent / trifluoroacetic acid; D2O / 96 h 19.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 18 steps 1.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 2.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 3.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 4.1: NaBH4 / methanol / 0.25 h / -78 °C 5.1: Et3N; MeOH / 28.8 h / 15 °C 6.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 6.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 7.1: Pd(OH)2/C / methanol / 12 h / 20 °C 8.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 9.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 10.1: CAN / acetonitrile; H2O / 2 h / 85 °C 11.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 12.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 13.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 14.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 15.1: HCl; dioxane / 24 h 16.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 17.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 18.1: 66 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 41 steps 1.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C 2.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C 3.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C 4.1: NaBH4 / methanol / 0.25 h / 20 °C 5.1: (+/-)-CSA / acetone / 0.67 h / 20 °C 5.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C 6.1: 99 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 7.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 8.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 9.1: 1.60 g / benzene; methanol / 1 h / 20 °C 10.1: CH2Cl2 / 0.25 h / 0 °C 11.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 12.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 13.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 14.1: pyridine / 10 h / 50 °C 15.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 16.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 17.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 18.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 19.1: Ac2O; DMSO / 2 h / 20 °C 20.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 21.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 22.1: 89 percent / TFA / methanol / 3 h / 20 °C 23.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 24.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 25.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 26.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 27.1: NaBH4 / methanol / 0.25 h / -78 °C 28.1: Et3N; MeOH / 28.8 h / 15 °C 29.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 29.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 30.1: Pd(OH)2/C / methanol / 12 h / 20 °C 31.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 32.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 33.1: CAN / acetonitrile; H2O / 2 h / 85 °C 34.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 35.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 36.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 37.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 38.1: HCl; dioxane / 24 h 39.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 40.1: 18 percent / Et3N / aq. methanol / 8 h / 20 °C 41.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 42 steps 1.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C 2.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C 3.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C 4.1: NaBH4 / methanol / 0.25 h / 20 °C 5.1: (+/-)-CSA / acetone / 0.67 h / 20 °C 5.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C 6.1: 99 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 7.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 8.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 9.1: 1.60 g / benzene; methanol / 1 h / 20 °C 10.1: CH2Cl2 / 0.25 h / 0 °C 11.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 12.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 13.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 14.1: pyridine / 10 h / 50 °C 15.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 16.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 17.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 18.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 19.1: Ac2O; DMSO / 2 h / 20 °C 20.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 21.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 22.1: 89 percent / TFA / methanol / 3 h / 20 °C 23.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 24.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 25.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 26.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 27.1: NaBH4 / methanol / 0.25 h / -78 °C 28.1: Et3N; MeOH / 28.8 h / 15 °C 29.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 29.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 30.1: Pd(OH)2/C / methanol / 12 h / 20 °C 31.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 32.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 33.1: CAN / acetonitrile; H2O / 2 h / 85 °C 34.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 35.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 36.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 37.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 38.1: HCl; dioxane / 24 h 39.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 40.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 41.1: 15 percent / trifluoroacetic acid; D2O / 96 h 42.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 41 steps 1.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C 2.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C 3.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C 4.1: NaBH4 / methanol / 0.25 h / 20 °C 5.1: (+/-)-CSA / acetone / 0.67 h / 20 °C 5.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C 6.1: 99 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 7.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 8.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 9.1: 1.60 g / benzene; methanol / 1 h / 20 °C 10.1: CH2Cl2 / 0.25 h / 0 °C 11.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 12.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 13.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 14.1: pyridine / 10 h / 50 °C 15.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 16.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 17.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 18.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 19.1: Ac2O; DMSO / 2 h / 20 °C 20.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 21.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 22.1: 89 percent / TFA / methanol / 3 h / 20 °C 23.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 24.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 25.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 26.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 27.1: NaBH4 / methanol / 0.25 h / -78 °C 28.1: Et3N; MeOH / 28.8 h / 15 °C 29.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 29.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 30.1: Pd(OH)2/C / methanol / 12 h / 20 °C 31.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 32.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 33.1: CAN / acetonitrile; H2O / 2 h / 85 °C 34.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 35.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 36.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 37.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 38.1: HCl; dioxane / 24 h 39.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 40.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 41.1: 66 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 43 steps 1.1: i-Pr2NEt; DMAP / 1,2-dichloro-ethane / 4 h / 60 °C 2.1: (+/-)-CSA; MeOH / 1 h / 20 °C 3.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C 4.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C 5.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C 6.1: NaBH4 / methanol / 0.25 h / 20 °C 7.1: (+/-)-CSA / acetone / 0.67 h / 20 °C 7.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C 8.1: 99 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 9.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 10.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 11.1: 1.60 g / benzene; methanol / 1 h / 20 °C 12.1: CH2Cl2 / 0.25 h / 0 °C 13.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 14.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 15.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 16.1: pyridine / 10 h / 50 °C 17.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 18.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 19.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 20.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 21.1: Ac2O; DMSO / 2 h / 20 °C 22.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 23.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 24.1: 89 percent / TFA / methanol / 3 h / 20 °C 25.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 26.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 27.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 28.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 29.1: NaBH4 / methanol / 0.25 h / -78 °C 30.1: Et3N; MeOH / 28.8 h / 15 °C 31.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 31.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 32.1: Pd(OH)2/C / methanol / 12 h / 20 °C 33.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 34.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 35.1: CAN / acetonitrile; H2O / 2 h / 85 °C 36.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 37.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 38.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 39.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 40.1: HCl; dioxane / 24 h 41.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 42.1: 18 percent / Et3N / aq. methanol / 8 h / 20 °C 43.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 44 steps 1.1: i-Pr2NEt; DMAP / 1,2-dichloro-ethane / 4 h / 60 °C 2.1: (+/-)-CSA; MeOH / 1 h / 20 °C 3.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C 4.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C 5.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C 6.1: NaBH4 / methanol / 0.25 h / 20 °C 7.1: (+/-)-CSA / acetone / 0.67 h / 20 °C 7.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C 8.1: 99 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 9.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 10.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 11.1: 1.60 g / benzene; methanol / 1 h / 20 °C 12.1: CH2Cl2 / 0.25 h / 0 °C 13.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 14.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 15.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 16.1: pyridine / 10 h / 50 °C 17.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 18.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 19.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 20.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 21.1: Ac2O; DMSO / 2 h / 20 °C 22.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 23.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 24.1: 89 percent / TFA / methanol / 3 h / 20 °C 25.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 26.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 27.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 28.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 29.1: NaBH4 / methanol / 0.25 h / -78 °C 30.1: Et3N; MeOH / 28.8 h / 15 °C 31.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 31.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 32.1: Pd(OH)2/C / methanol / 12 h / 20 °C 33.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 34.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 35.1: CAN / acetonitrile; H2O / 2 h / 85 °C 36.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 37.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 38.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 39.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 40.1: HCl; dioxane / 24 h 41.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 42.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 43.1: 15 percent / trifluoroacetic acid; D2O / 96 h 44.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 43 steps 1.1: i-Pr2NEt; DMAP / 1,2-dichloro-ethane / 4 h / 60 °C 2.1: (+/-)-CSA; MeOH / 1 h / 20 °C 3.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C 4.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C 5.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C 6.1: NaBH4 / methanol / 0.25 h / 20 °C 7.1: (+/-)-CSA / acetone / 0.67 h / 20 °C 7.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C 8.1: 99 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 9.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 10.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 11.1: 1.60 g / benzene; methanol / 1 h / 20 °C 12.1: CH2Cl2 / 0.25 h / 0 °C 13.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 14.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 15.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 16.1: pyridine / 10 h / 50 °C 17.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 18.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 19.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 20.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 21.1: Ac2O; DMSO / 2 h / 20 °C 22.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 23.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 24.1: 89 percent / TFA / methanol / 3 h / 20 °C 25.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 26.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 27.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 28.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 29.1: NaBH4 / methanol / 0.25 h / -78 °C 30.1: Et3N; MeOH / 28.8 h / 15 °C 31.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 31.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 32.1: Pd(OH)2/C / methanol / 12 h / 20 °C 33.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 34.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 35.1: CAN / acetonitrile; H2O / 2 h / 85 °C 36.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 37.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 38.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 39.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 40.1: HCl; dioxane / 24 h 41.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 42.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 43.1: 66 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
Benzoic acid (1S,5R,8S,8aR)-5-benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-1-hydroxymethyl-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 38 steps 1.1: NaBH4 / methanol / 0.25 h / 20 °C 2.1: (+/-)-CSA / acetone / 0.67 h / 20 °C 2.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C 3.1: 99 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 4.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 5.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 6.1: 1.60 g / benzene; methanol / 1 h / 20 °C 7.1: CH2Cl2 / 0.25 h / 0 °C 8.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 9.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 10.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 11.1: pyridine / 10 h / 50 °C 12.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 13.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 14.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 15.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 16.1: Ac2O; DMSO / 2 h / 20 °C 17.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 18.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 19.1: 89 percent / TFA / methanol / 3 h / 20 °C 20.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 21.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 22.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 23.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 24.1: NaBH4 / methanol / 0.25 h / -78 °C 25.1: Et3N; MeOH / 28.8 h / 15 °C 26.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 26.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 27.1: Pd(OH)2/C / methanol / 12 h / 20 °C 28.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 29.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 30.1: CAN / acetonitrile; H2O / 2 h / 85 °C 31.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 32.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 33.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 34.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 35.1: HCl; dioxane / 24 h 36.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 37.1: 18 percent / Et3N / aq. methanol / 8 h / 20 °C 38.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 39 steps 1.1: NaBH4 / methanol / 0.25 h / 20 °C 2.1: (+/-)-CSA / acetone / 0.67 h / 20 °C 2.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C 3.1: 99 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 4.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 5.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 6.1: 1.60 g / benzene; methanol / 1 h / 20 °C 7.1: CH2Cl2 / 0.25 h / 0 °C 8.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 9.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 10.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 11.1: pyridine / 10 h / 50 °C 12.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 13.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 14.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 15.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 16.1: Ac2O; DMSO / 2 h / 20 °C 17.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 18.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 19.1: 89 percent / TFA / methanol / 3 h / 20 °C 20.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 21.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 22.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 23.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 24.1: NaBH4 / methanol / 0.25 h / -78 °C 25.1: Et3N; MeOH / 28.8 h / 15 °C 26.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 26.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 27.1: Pd(OH)2/C / methanol / 12 h / 20 °C 28.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 29.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 30.1: CAN / acetonitrile; H2O / 2 h / 85 °C 31.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 32.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 33.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 34.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 35.1: HCl; dioxane / 24 h 36.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 37.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 38.1: 15 percent / trifluoroacetic acid; D2O / 96 h 39.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 38 steps 1.1: NaBH4 / methanol / 0.25 h / 20 °C 2.1: (+/-)-CSA / acetone / 0.67 h / 20 °C 2.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C 3.1: 99 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 4.1: 94 percent / K2CO3; Bu4NCl; NCS / TEMPO / CH2Cl2; aq. NaHCO3 / 0.5 h / 20 °C 5.1: 2-methyl-2-butene; aq. NaH2PO4; NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 6.1: 1.60 g / benzene; methanol / 1 h / 20 °C 7.1: CH2Cl2 / 0.25 h / 0 °C 8.1: 1.68 g / K2CO3 / methanol / 10 h / 0 °C 9.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C 10.1: LiBH4 / tetrahydrofuran / 3 h / 20 °C 11.1: pyridine / 10 h / 50 °C 12.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 13.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 14.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 15.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 16.1: Ac2O; DMSO / 2 h / 20 °C 17.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 18.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 19.1: 89 percent / TFA / methanol / 3 h / 20 °C 20.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 21.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 22.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 23.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 24.1: NaBH4 / methanol / 0.25 h / -78 °C 25.1: Et3N; MeOH / 28.8 h / 15 °C 26.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 26.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 27.1: Pd(OH)2/C / methanol / 12 h / 20 °C 28.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 29.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 30.1: CAN / acetonitrile; H2O / 2 h / 85 °C 31.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 32.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 33.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 34.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 35.1: HCl; dioxane / 24 h 36.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 37.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 38.1: 66 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
tetradotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 28 steps 1.1: pyridine / 10 h / 50 °C 2.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 3.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 4.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 5.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 6.1: Ac2O; DMSO / 2 h / 20 °C 7.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 8.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 9.1: 89 percent / TFA / methanol / 3 h / 20 °C 10.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 11.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 12.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 13.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 14.1: NaBH4 / methanol / 0.25 h / -78 °C 15.1: Et3N; MeOH / 28.8 h / 15 °C 16.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 16.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 17.1: Pd(OH)2/C / methanol / 12 h / 20 °C 18.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 19.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 20.1: CAN / acetonitrile; H2O / 2 h / 85 °C 21.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 22.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 23.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 24.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 25.1: HCl; dioxane / 24 h 26.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 27.1: 18 percent / Et3N / aq. methanol / 8 h / 20 °C 28.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 29 steps 1.1: pyridine / 10 h / 50 °C 2.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 3.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 4.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 5.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 6.1: Ac2O; DMSO / 2 h / 20 °C 7.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 8.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 9.1: 89 percent / TFA / methanol / 3 h / 20 °C 10.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 11.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 12.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 13.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 14.1: NaBH4 / methanol / 0.25 h / -78 °C 15.1: Et3N; MeOH / 28.8 h / 15 °C 16.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 16.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 17.1: Pd(OH)2/C / methanol / 12 h / 20 °C 18.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 19.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 20.1: CAN / acetonitrile; H2O / 2 h / 85 °C 21.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 22.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 23.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 24.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 25.1: HCl; dioxane / 24 h 26.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 27.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 28.1: 15 percent / trifluoroacetic acid; D2O / 96 h 29.1: 63 percent / trifluoroacetic acid; D2O / 96 h View Scheme | |
Multi-step reaction with 28 steps 1.1: pyridine / 10 h / 50 °C 2.1: 2.15 g / Et3N; DMAP / tetrahydrofuran / 48 h / 20 °C 3.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C 4.1: 98 percent / Na2HPO4; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C 5.1: 95 percent / Et3N / CH2Cl2 / 0.67 h / -42 °C 6.1: Ac2O; DMSO / 2 h / 20 °C 7.1: 1.04 g / NaBH4 / methanol / 0.25 h / 0 °C 8.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C 9.1: 89 percent / TFA / methanol / 3 h / 20 °C 10.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C 11.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C 12.1: NMO; OsO4 / acetone; H2O / 3 h / 20 °C 13.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C 14.1: NaBH4 / methanol / 0.25 h / -78 °C 15.1: Et3N; MeOH / 28.8 h / 15 °C 16.1: pyridine; Et3N / CH2Cl2 / 0.5 h / 0 °C 16.2: pyridine; DMAP / CH2Cl2 / 2 h / 20 °C 17.1: Pd(OH)2/C / methanol / 12 h / 20 °C 18.1: 96 mg / DMAP / pyridine / 2 h / 20 °C 19.1: 75 percent / aq. TFA / methanol; H2O / 26.4 h / 20 °C 20.1: CAN / acetonitrile; H2O / 2 h / 85 °C 21.1: 38.5 mg / Et3N; HgCl2 / dimethylformamide / 2 h / 20 °C 22.1: NaIO4 / methanol; H2O / 0.5 h / 20 °C 23.1: 22.9 mg / TFA / methanol / 1.5 h / 20 °C 24.1: aq. HCl / tetrahydrofuran / 24 h / 20 °C 25.1: HCl; dioxane / 24 h 26.1: 11.2 mg / Et3N / pyridine / 12 h / 40 °C 27.1: 67 percent / Et3N / aq. methanol / 8 h / 20 °C 28.1: 66 percent / trifluoroacetic acid; D2O / 96 h View Scheme |
Conditions | Yield |
---|---|
Stage #1: acetone With methanol; acetyl chloride at 20℃; for 0.5h; Stage #2: tetradotoxin for 26 - 192h; Product distribution / selectivity; | A 22% B 47% |
Conditions | Yield |
---|---|
Stage #1: methanol; acetone With acetyl chloride at 20℃; for 0.5h; Stage #2: tetradotoxin for 16h; Product distribution / selectivity; | 45% |
acetic anhydride
tetradotoxin
(5S)-8t-acetoxy-8c-acetoxymethyl-2-amino-(3at,7at,10bt)-3a,7a,8,9,10,10b-hexahydro-1(3)H-5r,10ac-cyclo-6c,9c-epioxido-[1,4]dioxepino[5,6,7-de]quinazoline-6,10c-diol
Conditions | Yield |
---|---|
(i) TsOH, (ii) Py, (iii) aq. NH3; Multistep reaction; |
tetradotoxin
4,9-anhydrotetrodotoxin
Conditions | Yield |
---|---|
(i) Ac2O, TsOH, (ii) Py, (iii) aq. NH3; Multistep reaction; |
tetradotoxin
(5R)-2,4c-diamino-12-hydroxymethyl-(4ac)-1(3),4,4a,5,9,10-hexahydro-5r,9c;7t,10at-dimethano-[1,3]dioxocino[6,5-d]pyrimidine-7,10t,11syn,12syn-tetraol
Conditions | Yield |
---|---|
(i) Ac2O, TsOH, (ii) Py, (iii) aq. NH3; Multistep reaction; |
tetradotoxin
(7S)-2-amino-4c,5t,10t,11anti-tetrahydroxy-(4ac)-1(3),4,4a,5-tetrahydro-7r,10ac-methano-oxocino[4,5-d]pyrimidine-6,9-dione
Conditions | Yield |
---|---|
With sulfuric acid; periodic acid at 0℃; |
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