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Cas:13096-62-3
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inquiryWelcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our
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inquiryManufacturer supply 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone CAS 13096-62-3 with superior quality Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical &a
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inquiryCangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new ap
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inquiryHigh quality. Factory supply. In stock. Best price.1.Quick response within 24 hours;2.Best quality in your requirement;?3.We pay more attention on delivery time, and usually ship on time;4.Under the premise of safety and effectiveness, we can produce
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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
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inquiryOur company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.
Cas:13096-62-3
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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
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inquiry2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone CAS No.:13096-62-3 HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture. With about ten years of business experiences on the mar
Cas:13096-62-3
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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
Cas:13096-62-3
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inquiry2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE Basic information Product Name: 2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE Synonyms: 2,3,4,6-TETRAKIS-O-(PHENYLMETHYL)-D-GLUCONIC ACID LACTONE;2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE;5-lactone
Cas:13096-62-3
Min.Order:100 Gram
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inquiry2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE CAS:13096-62-3 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
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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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inquiryNewCan Biotech Limited was established in 2021 and is primarily engaged in the research, development, production, and sales of sugars, nucleosides, nucleotides, phosphorylated monomers, as well as next-generation antiviral and antitumor drug intermed
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inquiryOur Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter
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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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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
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inquiry2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONEAppearance:as detail Storage:Room temperature Package:according to customers' requirements Application:Pharmaceutical Intermediates Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by sea(FOB or
Cas:13096-62-3
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inquiryProduct name: 2,3,4,6-Tetra-O-Benzyl-D-Glucono-1,5-Lactone CAS No.: 13096-62-3 Molecule Formula:C34H34O6 Molecule Weight:538.63 Purity: 97.0% Package: 5kg/drum Description:White or off-white powder Manufacture Standards:Enterprise Standard
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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,
Cas:13096-62-3
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inquiryOur 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
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inquiryHunan chemfish Pharmaceutical co.,Ltd.located in Lugu High-tech industral park ,Hunan province . with its own R&D center and more than 10000㎡manufacture plant . Chemfish owns 40 reactors from 1000L to 8000L. With complete auxiliary equipment as
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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
Cas:13096-62-3
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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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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
Cas:13096-62-3
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inquiryWe 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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inquiryStock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai
Cas:13096-62-3
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inquiryhigh purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:drum and bag Application:for pharma use Transportation:by sea or air Port:Beijing or Guangzhou
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inquiryR & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou
Cas:13096-62-3
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inquiry2,3,4,6-Tetra-O-benzyl-D-glucopyranose
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Solvent; | 100% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; | 100% |
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; | 100% |
2,3,4,6-tetra-O-benzyl-D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With acetic anhydride; dimethyl sulfoxide at 20℃; | 93% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside In dimethyl sulfoxide at 20 - 25℃; for 0.5h; Inert atmosphere; Stage #2: With acetic anhydride at 15 - 25℃; Inert atmosphere; | 92% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h; | 82% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 105h; Stage #2: With triethylamine In dichloromethane at -78 - 20℃; for 1h; |
2,3,4,6-tetra-O-benzyl-D-glucopyranose
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With acetic anhydride In dimethyl sulfoxide at 20℃; | 89% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: With tetrapropylammonium perruthenate In dichloromethane at 20℃; for 2h; | 82% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h; | 82% |
(2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Amberlite IR 120 H+ In 1,4-dioxane for 3h; Heating; | 88% |
2,3,4,6-tetra-O-benzoyl-D-glucopyranose
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Oxidation; | 85% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With palladium diacetate In acetonitrile at 80℃; for 2h; | 60% |
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
In benzene for 5h; Ambient temperature; Irradiation; | A 57% B 24% |
phenacyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
In benzene for 5h; Ambient temperature; Irradiation; | A 56% B 20% |
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
B
2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone
Conditions | Yield |
---|---|
In toluene at 110℃; Inert atmosphere; | A 45% B 45% |
2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
B
<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone
Conditions | Yield |
---|---|
With magnesium iodide In ethanol at 20℃; for 1h; | A 35% B 5% |
2,3,4,6-tetra-O-benzyl-β-1-C-(2-thiazolyl)-D-glucopyranose
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With 4 A molecular sieve In toluene at 130℃; for 14h; closed vial; Yield given; |
p-toluenesulfonyl chloride
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 3.5h; Title compound not separated from byproducts; |
methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TfOH / H2O 2: DMSO / acetic anhydride View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride; strontium (III) chloride hexahydrate / acetic acid; water / 70 °C 2: caesium carbonate; Iodine monochloride / dichloromethane / 3 h / 0 - 20 °C / Green chemistry View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; hydrogenchloride / water / 85 °C 2: acetic anhydride / dimethyl sulfoxide / 22 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid / Reflux 2: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid / water / 2 h / Reflux 2: acetic anhydride / dimethyl sulfoxide / 20 °C View Scheme |
methyl-alpha-D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid; acetic acid / water / 6 h / Reflux 2: acetic anhydride / dimethyl sulfoxide / 16 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: hydrogenchloride; strontium (III) chloride hexahydrate / acetic acid; water / 70 °C 3.1: caesium carbonate; Iodine monochloride / dichloromethane / 3 h / 0 - 20 °C / Green chemistry View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: acetic acid; hydrogenchloride / water / 85 °C 3.1: acetic anhydride / dimethyl sulfoxide / 22 h / 20 °C / Inert atmosphere View Scheme |
D-glucose pentaacetate
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: methanol; sodium methylate / 20 °C 2.2: Amberlite.(R). IR-120 H+ ion exchange 3.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere 3.2: 12 h / 20 °C / Inert atmosphere 4.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C 5.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C View Scheme | |
Multi-step reaction with 5 steps 1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 0 - 20 °C 2: sodium methylate; methanol 3: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C 4: N-iodo-succinimide; water / acetone 5: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme |
phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C 2: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C View Scheme |
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C 3.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C View Scheme |
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: methanol; sodium methylate / 20 °C 1.2: Amberlite.(R). IR-120 H+ ion exchange 2.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 3.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C 4.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C View Scheme |
2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 70 °C 1.2: 2 h / 20 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C 2.2: -78 - 0 °C View Scheme |
phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium methylate; methanol 2: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C 3: N-iodo-succinimide; water / acetone 4: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme |
phenyl 1-thio-D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C 2: N-iodo-succinimide; water / acetone 3: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme |
phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-iodo-succinimide; water / acetone 2: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme |
methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetic acid; water; sulfuric acid / 1 h / 110 °C 2: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride; acetic acid / water / 5 h / 100 °C / Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 48 h / 20 °C / Inert atmosphere; Molecular sieve View Scheme |
methyl D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.5 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 20 °C / Inert atmosphere 2.1: acetic acid; water; sulfuric acid / 1 h / 110 °C 3.1: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0.33 h / 55 °C 2: hydrogenchloride / tetrahydrofuran / 0.25 h / 20 °C 3: sodium hydroxide; dihydrogen peroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water / 0.17 h / 65 °C View Scheme |
benzyl bromide
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.5 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 20 °C / Inert atmosphere 2.1: acetic acid; water; sulfuric acid / 1 h / 110 °C 3.1: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: hydrogenchloride; strontium (III) chloride hexahydrate / acetic acid; water / 70 °C 3.1: caesium carbonate; Iodine monochloride / dichloromethane / 3 h / 0 - 20 °C / Green chemistry View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: acetic acid; hydrogenchloride / water / 85 °C 3.1: acetic anhydride / dimethyl sulfoxide / 22 h / 20 °C / Inert atmosphere View Scheme |
(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
B
2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere 2: toluene / 110 °C / Inert atmosphere View Scheme |
O-ethyl S-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl) dithiocarbonate
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
B
2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium / methanol / 2 h / 20 °C 2: triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere 3: toluene / 110 °C / Inert atmosphere View Scheme |
benzyl chloride
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0.33 h / 55 °C 2: hydrogenchloride / tetrahydrofuran / 0.25 h / 20 °C 3: sodium hydroxide; dihydrogen peroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water / 0.17 h / 65 °C View Scheme |
n-butyllithium
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
at -78℃; | 100% |
In tetrahydrofuran; toluene at -50℃; for 2h; | 72% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
phenyllithium
(2,3,4,6-tetra-O-benzyl-1-C-phenyl)-D-glucopyranose
Conditions | Yield |
---|---|
at -78℃; | 100% |
In tetrahydrofuran 1.) -78 deg C, 2 h, 2.) from -78 deg C to room temperature, 2 h; | 85.7% |
In tetrahydrofuran at -78℃; |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene at -20℃; | 100% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
(3R,4S,5R,6R)-3,4,5-trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-ethylbenzo[b]thiophen-2-yl-methyl)naphthalen-1-yl]tetrahydropyran-2-ol
Conditions | Yield |
---|---|
Stage #1: 2-(4-bromo-naphthalen-2-ylmethyl)-5-ethylbenzo[b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 0.0833333h; | 100% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
((3-bromo-4-fluorobenzyl)oxy)(tert-butyl)dimethylsilane
Conditions | Yield |
---|---|
Stage #1: ((3-bromo-4-fluorobenzyl)oxy)(tert-butyl)dimethylsilane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 1h; | 100% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 20℃; for 3h; | 99% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
1,3,5-trifluorobenzene
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trifluorobenzene With n-butyllithium In diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In diethyl ether at -78℃; for 0.25h; Inert atmosphere; Stage #3: With acetic acid In diethyl ether at -78℃; for 0.166667h; Inert atmosphere; | 98% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
2,3,4,6-tetra-O-benzyl-D-gluconamide
Conditions | Yield |
---|---|
With ammonia In methanol at 0℃; for 2h; | 97% |
With ammonia In methanol | 96% |
With ammonia In methanol at 0℃; for 3h; | 96% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
trans-2-propenyl bromide
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; | 97% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
propylene glycol
1,2-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-1,2-propanediol
Conditions | Yield |
---|---|
With sulfuric acid In benzene for 24h; Heating; | 96.2% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination; | 96% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone
Conditions | Yield |
---|---|
With sodium hydride; acetophenone In tetrahydrofuran 1.) 45 deg C, 30 min, 2.) 25 deg C, 5 min.; | 95% |
With sodium methylate In methanol for 0.5h; Ambient temperature; | 40 mg |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
dimethyl methane phosphonate
3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 1h; | 95% |
With n-butyllithium | 92% |
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.333333h; Metallation; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -70 - -40℃; for 1h; Addition; | 91% |
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78 - 0℃; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water; ethyl acetate cooling with ice; |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
tert-butyl 2-(bromomethyl)acrylate
Conditions | Yield |
---|---|
With samarium diiodide In tetrahydrofuran at 20℃; | 95% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
N-methoxylamine hydrochloride
Conditions | Yield |
---|---|
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination; | 95% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
ethyl acetate
2-deoxy-4,5,6,8-tetra-O-benzyl-α-D-gluco-3,7-pyranoso-3-octulosonate
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane | 95% |
Stage #1: ethyl acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -60℃; for 0.25h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -60 - 20℃; for 1h; Further stages.; | 66% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
benzylmagnesium chloride
1-C-benzyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose
Conditions | Yield |
---|---|
95% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
phenylmagnesium bromide
1-C-benzyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at -78 - -40℃; for 2h; | 95% |
n-butyllithium
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
2,3,4,6-tetra-O-benzyl-1-C-n-butyl-α-D-glucopyranose
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: With water In tetrahydrofuran; hexane Further stages.; | 95% |
In tetrahydrofuran; hexane at -78℃; for 0.5h; diastereoselective reaction; | 92% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
allyl bromide
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; zinc In tetrahydrofuran at 20℃; for 4h; Barbier Coupling Reaction; | 95% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
dichloromethane
2,3,4,6-Tetra-O-benzyl-1-C-(dichloromethyl)-α-D-glucopyranose
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane at -75 - -70℃; for 1h; | 94% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
2,2-Dimethyl-1,3-propanediol
2,3,4,6-tetra-O-benzyl-5',5'-dimethylspiro[1,5-anhydro-D-glucitol-1,2'-[1,3]dioxane]
Conditions | Yield |
---|---|
With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate In toluene at 20℃; for 1h; | 94% |
With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate In toluene at 20℃; for 2h; Cycloaddition; | 94% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
methyllithium
3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranose
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at -78℃; for 0.5h; diastereoselective reaction; | 94% |
In tetrahydrofuran; diethyl ether at -78℃; for 1h; | 83% |
In tetrahydrofuran at -78℃; for 0.166667h; | 67% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol
Conditions | Yield |
---|---|
In toluene | 94% |
In toluene at 65 - 70℃; for 14h; |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -50℃; | 93% |
With n-butyllithium In tetrahydrofuran at -50℃; for 1h; | 92% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
N-benzyloxyamine
1N-benzyloxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide
Conditions | Yield |
---|---|
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination; | 93% |
Stage #1: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; N-benzyloxyamine In dichloromethane at 20℃; for 0.5h; Stage #2: With trimethylaluminum In hexane; dichloromethane at 20℃; for 1h; Further stages.; | 93% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
O-ethylhydroxylamine hydrochloride
Conditions | Yield |
---|---|
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination; | 93% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
tert-butyl 4-iodobenzoate
Conditions | Yield |
---|---|
With n-butyllithium; 2,4,6-triisopropyl-1-bromobenzene In tetrahydrofuran at -78℃; for 1h; Reagent/catalyst; Barbier Coupling Reaction; Inert atmosphere; stereoselective reaction; | 93% |
Stage #1: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; tert-butyl 4-iodobenzoate With 2,4,6-triisopropylphenyl lithium In tetrahydrofuran at -78℃; Stage #2: With ammonium chloride In water | 93% |
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