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
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inquiryhigh quality Appearance:White or off-white Solid Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea Port:shanghai
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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
Cas:120205-50-7
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FOB Price: $1.2 / 5.0
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inquiryWITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et
Cas:120205-50-7
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inquiryN-Boc-(2R,3R,4S)-dolaproine CAS:120205-50-7 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality orga
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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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inquiryHenan 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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inquiryJ&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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inquirylow price high quality high purity good sevice stock Appearance:white Storage:Preserve In Well-Closed, Light-Resistant and Tight Containers. Store In Cool & Dry Place Package:1g,5g,10g...1kg,5kg...more Application:Pharmaceutical intermediat
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inquiryZibo 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
Product 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,
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Min.Order:1 Gram
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inquiryGMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,
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Min.Order:1 Milligram
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inquiryWe Huarong Pharm can provide Customized Synthesis & Process R&D & APIs and intermediates Production & Quality Research & Registration Application, especially our GMP validation service which complies with SFDA, FDA, WHO and EU EMPA. O
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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
Cas:120205-50-7
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inquiryWuhu Nuovo Chemical Technology Co., Ltd. was established in August 2014, mainly engaged in the development, production and sales of ionic liquids, ribose, nucleosides, nucleotides and related chemicals; Products are mainly used in new energy, new ma
Cas:120205-50-7
Min.Order:100 Gram
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Type:Manufacturers
inquiryHigh quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:This product can be use
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inquiryStock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai
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inquiryThe process is mature and can be mass produced to 100 kg, with good quality and purity up to 99%.The product has a large stock and can be supplied stably. Package:bottle Application:Drug R&D Transportation:Sealed drying(25℃) Port:ShangHai
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inquiryAcmec is a leading manufacturer and supplier of biochemical reagents and life science products. We have over 40,000 items in stock (real-time inventory) and offer discounted prices to registered members of the online store ( www.acmec.com.cn ) Appea
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Min.Order:1 bottle
Negotiable
Type:Lab/Research institutions
inquiry1.Our services:A.Supply sampleB.The packing also can be according the customers` requirmentC.Any inquiries will be replied within 24 hoursD.we provide Commerical Invoice, Packing List, Bill of loading, COA , Health certificate and Origin certificate.
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inquiryAnsciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali
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inquiryFactory supply high purity low priceAppearance:solid or liquid Storage:sealed in cool and dry place Package:As customer's requested Application:Pharma Intermediate Transportation:by courier/air/sea Port:Any port in China
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inquirySupply top quality products with a reasonable price Application:api
((2R,3R)-3-((S)-1-(tertbutoxycarbonyl)pyrrolidin-2-yl)-3-Methoxy-2-Methylpropanoic acidAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:pharmaceutical intermediate Transportation:by air
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inquiryfactory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
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inquiryApplication:thermoplastic elastomers, unsaturated polyesters, acrylics
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Min.Order:0 Metric Ton
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inquiryGood Quality Package:1kg/bag Application:Medical or chemical Transportation:Air/Train/Sea Port:Shenzhen
bulk?production Application:Pharmaceutical intermediates
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inquiryfactory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
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inquiryN-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Stage #1: (S)-t-butyl 2-((1R,2R)-1-methoxy-2-methyl-3-oxo-3-((R)-2-oxo-4-phenyloxazolidin-3-yl)propyl)pyrrolidine-1-carboxylate With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran at 0℃; for 3h; Stage #2: With sodium sulfite In tetrahydrofuran at 20 - 25℃; for 16h; | 99% |
(4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Stage #1: (4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone With dihydrogen peroxide In tetrahydrofuran; water at 0℃; for 0.0833333h; Stage #2: With water; lithium hydroxide In tetrahydrofuran at 0℃; for 3h; | 98% |
With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water at 0℃; for 3h; | 98% |
Stage #1: (4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone With dihydrogen peroxide In tetrahydrofuran; water at 0℃; for 0.0833333h; Stage #2: With lithium hydroxide In tetrahydrofuran; water at 0℃; for 3h; | 98% |
<2S-<2R*<(R*),α(S*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-methoxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol for 12h; Ambient temperature; | 94% |
ethyl (2R,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methyl-propanoate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With lithium hydroxide In ethanol | 91% |
With lithium hydroxide In ethanol; water at 20℃; | 59% |
With lithium hydroxide In ethanol at 20℃; | 59% |
(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid
methyl iodide
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Stage #1: (2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at 0℃; | 91% |
With sodium hydride In tetrahydrofuran at 0℃; for 18h; | 89% |
Stage #1: (2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid; methyl iodide With sodium hydride In tetrahydrofuran at -5 - 0℃; for 75h; Stage #2: With potassium hydrogensulfate In water pH=2; | 72% |
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Stage #1: C24H34N2O6 With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran for 4h; Stage #2: With sodium thiosulfate In tetrahydrofuran | 91% |
tert-butyl (2S)-2-((1R,2R)-1,3-dimethoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran; water at 20℃; for 16h; | 86% |
(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-methoxy-2'-methyl-3'-butenyl)-pyrrolidine
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With ruthenium(IV) oxide; sodium periodate In tetrachloromethane; water; acetonitrile for 48h; | 81% |
With ruthenium(IV) oxide; sodium periodate In tetrachloromethane; acetonitrile at 20℃; for 72h; | 75% |
Multi-step reaction with 2 steps 1: NaIO4, 60 percent aq. RuO2 / acetonitrile; CCl4 / 6 h 2: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.25 h View Scheme | |
Stage #1: (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-methoxy-2'-methyl-3'-butenyl)-pyrrolidine With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; tert-butyl alcohol for 12h; Stage #2: With sodium periodate; sodium permanganate In water; acetonitrile at 0 - 5℃; for 4h; | |
Multi-step reaction with 2 steps 1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 6 h / 20 °C 2: sodium periodate; potassium permanganate / water / 6 h / 0 °C View Scheme |
(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid
A
N-Boc-(2R,3R,4S)-dolaproine
C
[L-(trans)]-N-(t-butoxycarbonyl)-2-[2'-carboxy-2'-methyl-1'-ethenyl]pyrrolidine
Conditions | Yield |
---|---|
With sodium hydride; methyl iodide In tetrahydrofuran at 0℃; for 48h; | A 76% B 5.3% C 5.6% |
(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid
methyl iodide
A
N-Boc-(2R,3R,4S)-dolaproine
C
[L-(trans)]-N-(t-butoxycarbonyl)-2-[2'-carboxy-2'-methyl-1'-ethenyl]pyrrolidine
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0℃; for 48h; | A 76% B 5.3% C 5.6% |
(S)-2-[(1R,2R)-1-Methoxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal |
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With potassium permanganate In tert-butyl alcohol for 0.25h; Yield given; | |
With sodium chlorite; sodium dihydrogenphosphate dihydrate In tert-butyl alcohol at 20℃; for 8h; | 472 mg |
benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In water; tert-butyl alcohol |
ethyl (2R,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 45 percent / LHMDS; HMPA / tetrahydrofuran / 0.25 h / -20 °C 2: 59 percent / LiOH*H2O / ethanol; H2O / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1) LHMDS / 1) THF, HMPA 2: 91 percent / aq.LiOH / ethanol View Scheme |
Boc-L-Pro-H
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: DABCO / CH2Cl2 / 120 h / 20 °C / ultrasound 2: H2 / Pd/C / ethyl acetate / 20 °C 3: 70 percent / proton sponge / CH2Cl2 / 18 h / 20 °C 4: 86 percent / LiOH / tetrahydrofuran; H2O / 16 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: 70 percent / Co[P(Ph)3]4 / tetrahydrofuran / 2 h / 0 °C 2.1: 86 percent / 4 Angstroem molecular sieves; proton sponge / CH2Cl2 / 48 h / 20 °C 3.1: aq. H2O2; LiOH*H2O / tetrahydrofuran / 3 h / 0 °C 3.2: 94 percent / sodium sulfite / tetrahydrofuran / 18 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 1.) Et3N, (Bu)2BOTf, 2.) phosphate buffer, 30percent aq. H2O2 2: 1.) aq. H2O2, LiOH, 2.) aq. Na2SO3 / 1.) THF, 3 deg C, 5 h, 2.) THF, 25 deg C, 16 h 3: 76 percent / NaH, MeI / tetrahydrofuran / 48 h / 0 °C View Scheme |
(S)-2-((1R,2R)-1-Hydroxy-2-methoxycarbonyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / proton sponge / CH2Cl2 / 18 h / 20 °C 2: 86 percent / LiOH / tetrahydrofuran; H2O / 16 h / 20 °C View Scheme |
tert-butyl 2-(2-(methoxycarbonyl)-1-hydroxyallyl)pyrrolidine-1-carboxylate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2 / Pd/C / ethyl acetate / 20 °C 2: 70 percent / proton sponge / CH2Cl2 / 18 h / 20 °C 3: 86 percent / LiOH / tetrahydrofuran; H2O / 16 h / 20 °C View Scheme |
(4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3"-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 86 percent / 4 Angstroem molecular sieves; proton sponge / CH2Cl2 / 48 h / 20 °C 2.1: aq. H2O2; LiOH*H2O / tetrahydrofuran / 3 h / 0 °C 2.2: 94 percent / sodium sulfite / tetrahydrofuran / 18 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1.) aq. H2O2, LiOH, 2.) aq. Na2SO3 / 1.) THF, 3 deg C, 5 h, 2.) THF, 25 deg C, 16 h 2: 76 percent / NaH, MeI / tetrahydrofuran / 48 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: 83 percent / molecular sieves 4A, proton sponge / CH2Cl2 / 48 h / 0 - 20 °C 2: 1.) aq. H2O2, LiOH, 2.) aq. Na2SO3 / 1.) THF, 0 deg C, 3 h, 2.) THF, RT, 12 h View Scheme |
benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 41 percent / BF3*OEt2 / CH2Cl2 2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O View Scheme | |
Multi-step reaction with 2 steps 1: 94 percent / NaH / dimethylformamide / 0.5 h / 0 °C 2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O View Scheme |
1-(tert-butoxycarbonyl)-L-proline
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h 2: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C 3: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h 4: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C 5: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 6: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 6 steps 1: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h 2: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C 3: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h 4: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature 5: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 6: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 6 steps 1: 82 percent / BOP, DIEA / CH2Cl2 2: 89 percent / AlLiH4 / tetrahydrofuran / 1 h / Ambient temperature 3: 72 percent / tetrahydrofuran / 3 h / Ambient temperature 4: 90 percent / NaH / dimethylformamide / 24 h / Ambient temperature 5: NaIO4, 60 percent aq. RuO2 / acetonitrile; CCl4 / 6 h 6: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.25 h View Scheme |
di-tert-butyl dicarbonate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 95 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C 2: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h 3: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C 4: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h 5: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C 6: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 7: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 7 steps 1: 95 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C 2: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h 3: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C 4: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h 5: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature 6: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 7: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme |
N-(tert-butoxycarbonyl)-L-prolinol
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C 2: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h 3: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C 4: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 5: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 5 steps 1: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C 2: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h 3: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature 4: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 5: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1.1: triethylamine; dimethyl sulfoxide / 0.25 h / 5 - 10 °C 1.2: 2 h / 0 °C 2.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.75 h / 0 °C 2.2: 3 h / -78 - 25 °C 2.3: 1 h / 0 °C 3.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 48 h / 0 - 25 °C / Molecular sieve 4.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran / 3 h / 0 °C 4.2: 16 h / 20 - 25 °C View Scheme |
<2S-<2R*<(R*),α(R*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-hydroxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C 2: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 3: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature 2: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 3: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme |
<2S-<2R*<(R*),α(R*),β(S*)>>>-1-<(1,1-Dimethylethoxy)carbonyl>-β-methoxy-α-methyl-2-pyrrolidinepropanoic acid 2-hydroxy-1,2,2-triphenylethyl ester
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 2: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme |
L-proline
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 95 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C 2: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h 3: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C 4: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h 5: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C 6: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 7: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 7 steps 1: 95 percent / Et3N / CH2Cl2 / 2.5 h / 0 °C 2: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h 3: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C 4: 1.) i-Pr2N, n-BuLi, MgBr2*Et2O / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h; -78 deg C, 1 h, 2.) THF, -95 deg C, 2 h 5: 63 percent / proton sponge / CH2Cl2 / 46 h / Ambient temperature 6: 57 percent / potassium tert-butoxide / tetrahydrofuran / 0.08 h / -20 - -15 °C 7: 94 percent / H2 / 10percent Pd/C / methanol / 12 h / Ambient temperature View Scheme |
tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 89 percent / AlLiH4 / tetrahydrofuran / 1 h / Ambient temperature 2: 72 percent / tetrahydrofuran / 3 h / Ambient temperature 3: 90 percent / NaH / dimethylformamide / 24 h / Ambient temperature 4: NaIO4, 60 percent aq. RuO2 / acetonitrile; CCl4 / 6 h 5: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.25 h View Scheme |
(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / NaH / dimethylformamide / 24 h / Ambient temperature 2: NaIO4, 60 percent aq. RuO2 / acetonitrile; CCl4 / 6 h 3: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.25 h View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; hexane; N,N-dimethyl-formamide / 2 h / 0 - 5 °C 2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 12 h 2.2: 4 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.67 h / 0 - 20 °C / Inert atmosphere 2: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 6 h / 20 °C 3: sodium periodate; potassium permanganate / water / 6 h / 0 °C View Scheme |
(S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: BF3*Et2O 2: 57 percent / potassium tert-butoxide / tetrahydrofuran / -20 °C 3: H2 / Pd/C View Scheme |
(S)-2-[(1R,2S)-1-Methoxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 57 percent / potassium tert-butoxide / tetrahydrofuran / -20 °C 2: H2 / Pd/C View Scheme |
(S)-tert-butyl 2-((R)-3-ethoxy-1-hydroxy-3-oxopropyl)pyrrolidine-1-carboxylate
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1) LDA / 1) THF, HMPA, -78 deg C, 2) -78 deg C to -20 deg C, 2.5 h 2: 1) LDA, 2) MeOH / 1) THF, -20 deg C, 1 h, 2) -78 deg C 3: 1) LHMDS / 1) THF, HMPA 4: 91 percent / aq.LiOH / ethanol View Scheme |
(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine
N-Boc-(2R,3R,4S)-dolaproine
tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 75h; | 100% |
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide 1) 0 deg C, 2 h, 2) RT; | 98% |
With triethylamine; diethyl dicarbonate In N,N-dimethyl-formamide | 97.5% |
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 81% |
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere; | 81% |
N-Boc-(2R,3R,4S)-dolaproine
diazomethyl-trimethyl-silane
tert-butyl (2S)-2-((1R,2R)-1,3-dimethoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
In methanol; diethyl ether; hexane at 0 - 20℃; for 0.166667h; | 100% |
methanol
N-Boc-(2R,3R,4S)-dolaproine
(2R,3R)-3-methoxy-2-methyl-3-((S)-pyrrolidin-2-yl)propanoic acid methyl ester
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; | 100% |
With thionyl chloride at 0 - 20℃; | 44 mg |
ethanol
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; for 18h; | 100% |
With thionyl chloride at 0 - 20℃; for 18h; | 100% |
N-Boc-(2R,3R,4S)-dolaproine
(2R,3R)-3-methoxy-2-methyl-3-((S)-pyrrolidin-2-yl)propanoic acid methyl ester
Conditions | Yield |
---|---|
With thionyl chloride In methanol at 20℃; | 100% |
(1S,2R)-(+)-norphedrine
N-Boc-(2R,3R,4S)-dolaproine
tert-butyl (2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere; | 98% |
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere; | 98% |
With diethyl cyanophosphonate; triethylamine at 0 - 20℃; for 6h; Inert atmosphere; | 98% |
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 98% |
(1S,2R)-(+)-norphedrine
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 95% |
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
Stage #1: N-Boc-(2R,3R,4S)-dolaproine With hydrogenchloride at 20℃; for 6h; Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(3R,4S,5S)-3-methoxy-5-methyl-1-oxo-1-(pentafluorophenoxy)heptan-4-yl]-N-methyl-L-valinamide With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; | 92% |
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
N-Boc-(2R,3R,4S)-dolaproine
(S)-tert-butyl 2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 5.5h; Inert atmosphere; | 90% |
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 83% |
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 83% |
N-Boc-(2R,3R,4S)-dolaproine
(S)-2-(benzyloxy)-1-hydroxy-3-phenylpropane
Conditions | Yield |
---|---|
With dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 12h; | 86% |
N-Boc-(2R,3R,4S)-dolaproine
(S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-phenyl-propan-2-ol
(S)-2-{(1R,2R)-2-[(S)-1-Benzyl-2-(tert-butyl-diphenyl-silanyloxy)-ethoxycarbonyl]-1-methoxy-propyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 11h; | 85% |
methyl (2S)-2-amino-3-phenylpropanoate
N-Boc-(2R,3R,4S)-dolaproine
(S)-tert-butyl 2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 85% |
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 85% |
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 84% |
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; | 84% |
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 20 - 30℃; for 2h; Inert atmosphere; | 83.9% |
N-Boc-(2R,3R,4S)-dolaproine
(S)-tert-butyl 2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 83% |
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 83% |
N-Boc-(2R,3R,4S)-dolaproine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile at 23℃; for 12h; Inert atmosphere; | 82.6% |
tyrosamine
N-Boc-(2R,3R,4S)-dolaproine
N-Boc-Dap-4-hydroxyphenethylamide
Conditions | Yield |
---|---|
Stage #1: N-Boc-(2R,3R,4S)-dolaproine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: tyrosamine In N,N-dimethyl-formamide at 20℃; for 16h; | 82% |
Stage #1: N-Boc-(2R,3R,4S)-dolaproine With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: tyrosamine In N,N-dimethyl-formamide at 20℃; for 16h; | 82% |
N-Boc-(2R,3R,4S)-dolaproine
(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethanamine, hydrochloride salt
tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 20h; | 81% |
With triethylamine; diethyl dicarbonate In 1,2-dimethoxyethane at 4℃; for 14h; | 78% |
N-Boc-(2R,3R,4S)-dolaproine
tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 81% |
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 81% |
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 81% |
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