Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-
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inquiryDayangchem'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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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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inquiryProduct Name (-)-Corey Lactone Diol CAS Number 32233-40-2 Molecular Formula C8H12O4 Molecular Weight 172.18 Lot Size 10 kg TEST RESULTS Appearance - Colour O
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inquirySinoway ISO 9001:2008 CERTIFIED COMPANY SGS AUDITED COMPANY 34 years expereince in pharmaceutical industry Products High purity 99% up with low impurity below 0.1% Appearance:White crystalline powder Storage:2-8degree Package:ACCORDI
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inquiry1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; ...... Appearance:White Crystalline Powder Storage:-20°C Package:1kg/foil bag;
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inquiry(-)-Corey Lactone Diol CAS:32233-40-2 Name (-)-Corey lactone diol Synonyms (-)-6beta-Hydroxymethyl-7alpha-hydroxy-cis-2-oxabicyclo[3.3.0]octan-3-one; (3aR,4S,5R,6aS)-(-)-Hexahydro-5-hydroxy-4-(hydroxymethyl)-2H
Product description: Product name (-)-Corey lactone diol CAS number 32233-40-2 Assay ≥99% Appearance Off-white to brown crystalline powder Capacity 200mt/year Application Pha
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inquiryThe above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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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
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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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inquiry(-)-Corey lactone diol Basic information Product Name: (-)-Corey lactone diol Synonyms: COREY LACTONE DIOL;(3AR,4S,5R,6AS)-(-)-HEXAHYDRO-5-HYDROXY-4-(HYDROXYMETHYL)-2H-CYCLOPENT A[B]FURA
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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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inquiryName: (-)-Corey lactone diol Synonyms: COREY LACTONE DIOL CAS: 32233-40-2 MF: C8H12O4 Appearance:White powder Storage:Store in cool and dry place, away from sun light. Package:25kg/drum Application:Syntheses Material Intermediates Transportation:
PRODUCT DETAILS (-)-Corey Lactone Diol CAS No. 32233-40-2 Molecular Formula C8H12O4 Molecular Weight 172.18 TEST SPECIFICTIONS Description A white or almost white crystalline pow
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inquiry(-)-Corey lactone diol CAS:32233-40-2 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 organic in
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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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inquiryHangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det
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A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc
Cas:32233-40-2
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inquiry(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In dichloromethane at 20℃; for 0.833333h; atmospheric pressure; | 99% |
Multi-step reaction with 2 steps 1: 90 percent / PPTS / 1,2-dichloro-ethane / 2 h / Ambient temperature 2: 3,4-Dihydro-2H-pyran / TsOH View Scheme |
(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
Stage #1: (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one With sodium methylate In methanol at 20℃; for 1.5h; Stage #2: With hydrogenchloride In 1,4-dioxane; methanol at 20℃; pH=3 - 4; | 97% |
With sodium methylate In methanol at 20℃; for 2h; | 95% |
(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate In methanol at 100℃; for 0.25h; Microwave irradiation; | 96% |
With cerium (IV) sulfate tetrahydrate In methanol at 60℃; for 12h; | 96% |
With aluminium(III) chloride hexahydrate In methanol at 100℃; for 0.25h; Solvent; Microwave irradiation; Sealed tube; chemoselective reaction; | 95% |
(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With Amberlite IR 120 resin In methanol at 70℃; for 8h; | 86% |
(-)-Corey lactone 5-(4-phenylbenzoate)
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With potassium carbonate In methanol; dichloromethane for 3h; Ambient temperature; | 85% |
Multi-step reaction with 4 steps 1: 94 percent / imidazole / dimethylformamide / 1 h / Ambient temperature 2: 65 percent / CH3ONa / methanol / 1.33 h / Ambient temperature 3: 90 percent / PPTS / 1,2-dichloro-ethane / 2 h / Ambient temperature 4: 3,4-Dihydro-2H-pyran / TsOH View Scheme |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; methanol for 4h; Ambient temperature; | 83% |
(3aR,4S,5R,6aS)-5-(acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With Amberlite IR 120 resin In methanol at 70℃; for 8h; | 82% |
With hydrogenchloride In methanol; water for 4h; Reflux; | 82.1% |
With DBN In methanol at 20℃; for 12h; | |
With methanol at 25 - 65℃; | 28 g |
(1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With Amberlite IR 120 resin In methanol at 70℃; for 8h; | 82% |
With resin Wofatit SBW (OH-) In methanol for 2h; Ambient temperature; | 79% |
formaldehyd
(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
Stage #1: formaldehyd; (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one With formic acid; sulfuric acid at 80℃; for 24h; Stage #2: With potassium carbonate In methanol at 0 - 20℃; for 2h; | 79% |
(4aS,4bR,7aS,8aR)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
1,1-dimethoxyethane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol at 75 - 80℃; for 4h; | A 78% B n/a |
(E)-(4S,6R)-4,6-Dihydroxy-6-((S)-2-thioxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid methyl ester
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
(3aR,4R,5R,6aS)-(-)-5-hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating; Further byproducts given; | A 19% B 44% C 13% D 8% |
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating; | A 19% B 40% C n/a D n/a |
(E)-(4S,6R)-4,6-Dihydroxy-6-((S)-2-thioxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid methyl ester
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
(3aR,4R,5R,6aS)-(-)-5-hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating; Further byproducts given; | A 19% B 44% C 13% D 2% |
(E)-(4S,6R)-4,6-Dihydroxy-6-((S)-2-thioxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid methyl ester
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
(3aR,4R,5R,6aS)-(-)-5-hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating; Further byproducts given; | A 19% B 44% C 13% D 1% |
(1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one
C
<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one
D
(3aS,4R,5S,6aR)-5-acetoxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one
Conditions | Yield |
---|---|
With sodium hydroxide; Soerensen phosphate buffer In methanol at 36℃; for 24h; subtilisin DY; Further byproducts given. Yields of byproduct given; | A n/a B n/a C 20% D n/a |
With sodium hydroxide; Soerensen phosphate buffer In methanol at 36℃; for 24h; subtilisin DY; Further byproducts given. Yields of byproduct given; | A 16% B n/a C n/a D n/a |
3,4-dihydro-2H-pyran
(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one
Conditions | Yield |
---|---|
toluene-4-sulfonic acid Yields of byproduct given; | A n/a B 17% |
(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one
Conditions | Yield |
---|---|
With 3,4-dihydro-2H-pyran; toluene-4-sulfonic acid Yield given; | A n/a B 17% |
formaldehyd
(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
acetic anhydride
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
(4aS,4bR,7aS,8aR)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one
Conditions | Yield |
---|---|
With sodium hydroxide; sulfuric acid 1) 70 to 80 deg C, 20 h, sealed vessel, 2) 60 to 65 deg C, 40 h, sealed vessel, 3) RT, 20 h; Multistep reaction; |
Formic acid (3aR,4S,5R,6aS)-4-formyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With sodium methylate In methanol | |
With sodium In methanol at 0℃; for 0.5h; | 6.2 g |
(3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran at 25℃; Yield given; |
(1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one
C
<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one
D
(3aS,4R,5S,6aR)-5-acetoxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one
E
(1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one
F
(1R,5S,6S,7S)-(+)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 36℃; for 24h; Product distribution; subtilisin DY, Soerensen phosphate buffer pH 7, further solvents, further enzymes; |
2-oxa-3-oxo-6-syn-hydroxymethyl-7-anti-acetoxy-cis-bicyclo[3,3,0]octane
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one
Conditions | Yield |
---|---|
With Wofatit SBW In methanol for 2h; Ambient temperature; Title compound not separated from byproducts; |
2-oxa-3-oxo-6-syn-acetoxymethyl-7-anti-hydroxy-cis-bicyclo[3,3,0]octane
A
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
B
<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one
Conditions | Yield |
---|---|
With Wofatit SBW In methanol for 2h; Ambient temperature; Title compound not separated from byproducts; |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature; |
(1S,2S,6R,8S)-10,10-dimethyl-5,9,11-trioxatricyclo[6.4.0.02,6]dodecan-4-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With Dowex 50wX8 In tetrahydrofuran; water at 20℃; for 3h; |
6-oxabicyclo[3.1.0]hex-2-ene
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 70 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C 2: 0.95 g / 30percent H2O2, 30 percent KOH / ethanol / 1.) 45 deg C, 1 h, 2.) reflux, 6 h 3: 91 percent / HCL / 0.67 h 4: 80 percent / pyridine / 1 h / 0 °C 5: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C 6: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h 7: 6.2 g / sodium / methanol / 0.5 h / 0 °C View Scheme |
(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h 2: 6.2 g / sodium / methanol / 0.5 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: H2SO4 2: MeONa / methanol View Scheme | |
Multi-step reaction with 2 steps 1: 9.5 percent / glacial acetic acid, sulfuric acid / 24 h / 75 - 80 °C 2: 78 percent / p-toluenesulfonic acid / methanol / 4 h / 75 - 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid / 24 h / 50 - 80 °C / Sealed tube 2: DBN / methanol / 12 h / 20 °C View Scheme |
(-)-trans-2-carboxymethylcyclopent-3-en-1-ol
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 91 percent / HCL / 0.67 h 2: 80 percent / pyridine / 1 h / 0 °C 3: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C 4: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h 5: 6.2 g / sodium / methanol / 0.5 h / 0 °C View Scheme |
methyl 2R-methylsulfonyloxy-4-cyclopentene-1R-acetate
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C 2: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h 3: 6.2 g / sodium / methanol / 0.5 h / 0 °C View Scheme |
(-)-trans-2-methoxycarbonylmethylcyclopent-3-en-1-ol
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 80 percent / pyridine / 1 h / 0 °C 2: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C 3: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h 4: 6.2 g / sodium / methanol / 0.5 h / 0 °C View Scheme |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
trityl chloride
(-)-7α-hydroxy-6β-triphenylmethoxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere; | 100% |
With pyridine In dichloromethane | 93% |
With pyridine at 20℃; for 48h; | 87% |
In pyridine at 20℃; for 48h; Substitution; | 87% |
With pyridine at 20℃; for 12h; Temperature; Large scale; |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
triisopropylsilyl chloride
[(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4(triisopropylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one]
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane for 15h; | 100% |
Stage #1: (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one; triisopropylsilyl chloride With 1H-imidazole In dichloromethane for 15h; Stage #2: With hydrogenchloride In dichloromethane; water at 0℃; pH=3 - 4; | 100% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
tert-butyldimethylsilyl chloride
(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 3h; Inert atmosphere; | 100% |
With 1H-imidazole In dichloromethane at 0 - 40℃; for 24h; Inert atmosphere; | 95% |
With 1H-imidazole; dmap In dichloromethane at 0 - 30℃; for 16h; | 340 g |
With 1H-imidazole In dichloromethane at 40℃; Inert atmosphere; | 23 g |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
triisopropylsilyl trifluoromethanesulfonate
[(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4(triisopropylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one]
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 100% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
triethylsilyl chloride
(-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one
Conditions | Yield |
---|---|
With pyridine at 60℃; for 1h; | 97% |
With pyridine at 65℃; for 4h; | 94.55% |
With pyridine at 60℃; for 1h; | 93% |
With pyridine at 60℃; for 1h; | 93% |
With 1H-imidazole In N,N-dimethyl-formamide at 5℃; for 4h; Inert atmosphere; |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
tert-butyldimethylsilyl chloride
(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 10℃; for 2h; | 96.3% |
With 1H-imidazole In dichloromethane at 20℃; | 94.5% |
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 1h; | 89% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Corey aldehyde
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -78℃; for 1.03333h; Reagent/catalyst; Solvent; Temperature; | 95% |
With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -78℃; for 1h; Reagent/catalyst; Solvent; Temperature; | 95% |
With oxalyl dichloride; triethylamine In dimethyl sulfoxide |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
4-biphenyl-carboxylic acid chloride
(-)-Corey lactone 5-(4-phenylbenzoate)
Conditions | Yield |
---|---|
Stage #1: (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one With pyridine; trityl chloride at 20℃; for 12h; Large scale; Stage #2: 4-biphenyl-carboxylic acid chloride at 30℃; for 4.5h; Temperature; Large scale; | 93.45% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
triethylsilyl chloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 30℃; for 2h; Temperature; Solvent; Reagent/catalyst; | 92% |
methanol
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; for 7h; | 92% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
N,N-diethyl-1,1,1-trimethylsilanamine
7α-hydroxy-6β-hydroxymethylene-2-oxabicyclo<3.3.0>octan-3-one bistrimethylsilyl ether
Conditions | Yield |
---|---|
at 145℃; for 1h; | 90% |
vinyl acetate
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
(1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one
Conditions | Yield |
---|---|
With ALPS at 40℃; for 24h; | 90% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
t-butyldimethylsiyl triflate
(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In dichloromethane at -20 - 20℃; Inert atmosphere; | 89.4% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
p-Anisaldehyde dimethyl acetal
C16H18O5
Conditions | Yield |
---|---|
4-methoxybenzoic acid In toluene at 120℃; for 3h; Dean-Stark apparatus; | 87% |
3,4-dihydro-2H-pyran
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In dichloromethane for 1.5h; Ambient temperature; | 84% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
tert-butylchlorodiphenylsilane
(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4-[(tert-butyldiphenylsilyloxy)methyl]-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at -40℃; for 2h; | 84% |
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 2h; |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
tert-butyldimethylsilyl chloride
(3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 8h; Reagent/catalyst; | 83% |
With 1H-imidazole In dichloromethane at 20℃; for 8h; | 82% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
benzoyl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; enantioselective reaction; | 80% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
tert-butyldimethylsilyl chloride
A
(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one
B
(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane 1.) -20 deg C, 1.5 h, 2.) room temperature, 16 h; | A 76% B 4% |
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
p-toluenesulfonyl chloride
(3aR,4S,5R,6aS)-5-p-toluenesulfoxy-4-[(p-toluenesulfoxy)methyl]hexahydrocyclopenta[b]furan-2-one
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 3h; | 73% |
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