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Taizhou Crene Biotechnology co.ltd

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-

(-)-Corey lactone diol 32233-40-2

Cas:32233-40-2

Min.Order:1 Gram

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Type:Lab/Research institutions

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Dayang Chem (Hangzhou) Co.,Ltd.

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

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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Simagchem Corporation

Welcome 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

High quality Corey Lactone Diol supplier in China

Cas:32233-40-2

Min.Order:0 Metric Ton

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Type:Manufacturers

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Kono Chem Co.,Ltd

Product 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

CAS: 32233-40-2 (-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Kilogram

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Type:Other

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Sinoway Industrial Co., Ltd.

Sinoway 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

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Gram

FOB Price: $3000.0

Type:Trading Company

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Wuhan Fortuna Chemical Co.,Ltd

1. 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;

High quality (-)-Corey lactone diol CAS 32233-40-2 with factory price

Cas:32233-40-2

Min.Order:1 Kilogram

FOB Price: $20.0

Type:Trading Company

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Hangzhou Think Chemical Co. Ltd

(-)-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

(-)-Corey Lactone Diol stock

Cas:32233-40-2

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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Jinan Finer Chemical Co., Ltd

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

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:10 Gram

FOB Price: $12.0

Type:Lab/Research institutions

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Ality Chemical Corporation

The 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

Xi'an Xszo Chem Co., Ltd.

1. 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

Factory Price API 99% (-)-Corey lactone diol 32233-40-2 GMP Manufacturer

Cas:32233-40-2

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

Cangzhou 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

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Kilogram

FOB Price: $5.0 / 10.0

Type:Manufacturers

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Chemwill Asia Co., Ltd.

CHemwill -- (-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

(-)-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

TIANFU-CHEM CAS:32233-40-2 (-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Gram

FOB Price: $1000.0 / 1300.0

Type:Trading Company

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Zhuozhou Wenxi import and Export Co., Ltd

WITH 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

New production CAS 32233-40-2 with best quality

Cas:32233-40-2

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

TIANFUCHEM--High purity (-)-Corey lactone diol factory price

Cas:32233-40-2

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&amp

(-)-Corey lactone diol/ LIDE PHARMA- Factory supply / Best price

Cas:32233-40-2

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Henan Sinotech Import&Export Corporation

Name: (-)-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:

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

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Leader Biochemical Group

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

China Largest Factory Manufacturer sales (-)-Corey lactone diol CAS 32233-40-2

Cas:32233-40-2

Min.Order:1 Kilogram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

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Hubei Langyou International Trading Co., Ltd

Advantages: Hubei XinRunde Chemical Co., Ltd is a renowned pharmaceutical manufacturer. We can offer high quality products at competitive price in quick delivery with 100% custom pass guaranteed. Never stop striving to offer our best service is

(-)-Corey lactone diol CAS NO 32233-40-2

Cas:32233-40-2

Min.Order:1 Kilogram

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Type:Other

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Shanghai Upbio Tech Co.,Ltd

1.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

(-)-Corey lactone diol 32233-40-2

Cas:32233-40-2

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

Pharmaceutical Intermediate, (-)-Corey lactone diol CAS:32233-40-2

Cas:32233-40-2

Min.Order:1 Kilogram

FOB Price: $68.0 / 72.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

(-)-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

(-)-Corey lactone diol CAS:32233-40-2

Cas:32233-40-2

Min.Order:1 Gram

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Type:Lab/Research institutions

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Shandong Hanjiang Chemical Co., Ltd.

Hello, 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

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Wuhan Wonda Pharm Limited

1.high quality: quality is life. quality is the most important element for all goods. we have a lab doing research in wuhan china. hplc and nmr is available if needed. 2.reasonable price: we provide high quality products wi

Factory supply Corey Lactone Diol

Cas:32233-40-2

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

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Henan Wentao Chemical Product Co., Ltd.

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

CAS NO.:32233-40-2

Cas:32233-40-2

Min.Order:0

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Type:Lab/Research institutions

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Hebei Quanhe Biotechnology Co. LTD

1. Timely and efficient service to ensure communication with customers 2. Produce products of different specifications and sizes according to your requirements. 3. Quality procedures and standards recognized by SGS. Advanced plant equipment ensures s

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:1 Kilogram

FOB Price: $80.0 / 100.0

Type:Lab/Research institutions

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Hangzhou Keyingchem Co.,Ltd

Hangzhou 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

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:0 Metric Ton

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Type:Lab/Research institutions

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Afine Chemicals Limited

Our 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

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:0

Negotiable

Type:Lab/Research institutions

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SHANGHAI T&W PHARMACEUTICAL CO., LTD.

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

(-)-Corey lactone diol

Cas:32233-40-2

Min.Order:4 Kilogram

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Type:Lab/Research institutions

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Synthetic route

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one
58707-50-9, 72777-85-6, 81203-78-3, 65025-94-7

(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
39746-00-4

(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
117624-93-8

(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
26054-65-9

(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With Amberlite IR 120 resin In methanol at 70℃; for 8h;86%
(-)-Corey lactone 5-(4-phenylbenzoate)
31752-99-5

(-)-Corey lactone 5-(4-phenylbenzoate)

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
Biphenyl-4-carboxylic acid (3aR,4S,5R,6aS)-5-hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-ylmethyl ester

Biphenyl-4-carboxylic acid (3aR,4S,5R,6aS)-5-hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-ylmethyl ester

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
62939-82-6

(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
57930-46-8

(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
50-00-0

formaldehyd

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
26054-46-6

(-)-(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
109122-52-3

(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

1,1-dimethoxyethane
534-15-6

1,1-dimethoxyethane

Conditions
ConditionsYield
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
159812-78-9

(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
32233-40-2

(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
159812-79-0

(3aR,4R,5R,6aS)-(-)-5-hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one

C

(2S,6S,8R,9R)-8-Hydroxy-5,11,12-trioxa-tricyclo[7.2.1.02,6]dodecan-4-one

(2S,6S,8R,9R)-8-Hydroxy-5,11,12-trioxa-tricyclo[7.2.1.02,6]dodecan-4-one

D

((1R,2R,4S,5R)-2,4-Dihydroxy-7,9-dioxa-bicyclo[4.2.1]non-5-yl)-acetic acid methyl ester

((1R,2R,4S,5R)-2,4-Dihydroxy-7,9-dioxa-bicyclo[4.2.1]non-5-yl)-acetic acid methyl ester

Conditions
ConditionsYield
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
159812-78-9

(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
32233-40-2

(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
159812-79-0

(3aR,4R,5R,6aS)-(-)-5-hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one

C

(2S,6S,8R,9R)-8-Hydroxy-5,11,12-trioxa-tricyclo[7.2.1.02,6]dodecan-4-one

(2S,6S,8R,9R)-8-Hydroxy-5,11,12-trioxa-tricyclo[7.2.1.02,6]dodecan-4-one

D

(E)-(4S,6R,7S)-4,6,7,8-Tetrahydroxy-oct-2-enoic acid methyl ester

(E)-(4S,6R,7S)-4,6,7,8-Tetrahydroxy-oct-2-enoic acid methyl ester

Conditions
ConditionsYield
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
159812-78-9

(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
32233-40-2

(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
159812-79-0

(3aR,4R,5R,6aS)-(-)-5-hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one

C

(2S,6S,8R,9R)-8-Hydroxy-5,11,12-trioxa-tricyclo[7.2.1.02,6]dodecan-4-one

(2S,6S,8R,9R)-8-Hydroxy-5,11,12-trioxa-tricyclo[7.2.1.02,6]dodecan-4-one

D

(S)-4-[(R)-1-Hydroxy-2-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-[1,3]oxathiolan-2-one

(S)-4-[(R)-1-Hydroxy-2-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-[1,3]oxathiolan-2-one

Conditions
ConditionsYield
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
90529-18-3

(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
32233-40-2

(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
26054-65-9

(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
76704-05-7

<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
125226-81-5

(3aS,4R,5S,6aR)-5-acetoxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one

Conditions
ConditionsYield
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
110-87-2

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
65025-95-8

(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
32233-40-2

(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
67788-45-8

(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one

Conditions
ConditionsYield
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
65025-95-8

(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
32233-40-2

(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
67788-45-8

(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one

Conditions
ConditionsYield
With 3,4-dihydro-2H-pyran; toluene-4-sulfonic acid Yield given;A n/a
B 17%
formaldehyd
50-00-0

formaldehyd

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
26054-46-6

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

acetic anhydride
108-24-7

acetic anhydride

A

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(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
109122-52-3

(4aS,4bR,7aS,8aR)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one

Conditions
ConditionsYield
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
130325-32-5

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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
69222-61-3

(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 25℃; Yield given;
(1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one
90529-18-3

(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
32233-40-2

(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
26054-65-9

(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
76704-05-7

<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
125226-81-5

(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
57930-46-8

(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
125226-80-4

(1R,5S,6S,7S)-(+)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
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
51705-34-1, 39648-25-4

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
32233-40-2

(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
76704-05-7

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

Conditions
ConditionsYield
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
134732-93-7

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
32233-40-2

(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
76704-05-7

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

Conditions
ConditionsYield
With Wofatit SBW In methanol for 2h; Ambient temperature; Title compound not separated from byproducts;
(4aR,5S,7R,7aS)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-cyclopenta[c]pyran-3-one

(4aR,5S,7R,7aS)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-cyclopenta[c]pyran-3-one

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
315716-34-8

(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With Dowex 50wX8 In tetrahydrofuran; water at 20℃; for 3h;
6-oxabicyclo[3.1.0]hex-2-ene
7129-41-1

6-oxabicyclo[3.1.0]hex-2-ene

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
26054-46-6

(-)-(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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
49826-03-1

(-)-trans-2-carboxymethylcyclopent-3-en-1-ol

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
49826-01-9

methyl 2R-methylsulfonyloxy-4-cyclopentene-1R-acetate

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
49825-99-2

(-)-trans-2-methoxycarbonylmethylcyclopent-3-en-1-ol

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

trityl chloride
76-83-5

trityl chloride

(-)-7α-hydroxy-6β-triphenylmethoxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one
62939-85-9

(-)-7α-hydroxy-6β-triphenylmethoxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;100%
With pyridine In dichloromethane93%
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

[(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4(triisopropylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one]
1236109-24-2

[(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4(triisopropylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one]

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one
117624-93-8

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

[(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4(triisopropylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one]
1236109-24-2

[(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4(triisopropylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one]

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

triethylsilyl chloride
994-30-9

triethylsilyl chloride

(-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one
128948-09-4

(-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one
58707-50-9, 72777-85-6, 81203-78-3, 65025-94-7

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Corey aldehyde
62961-72-2

Corey aldehyde

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

4-biphenyl-carboxylic acid chloride
14002-51-8

4-biphenyl-carboxylic acid chloride

(-)-Corey lactone 5-(4-phenylbenzoate)
31752-99-5

(-)-Corey lactone 5-(4-phenylbenzoate)

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

triethylsilyl chloride
994-30-9

triethylsilyl chloride

C14H26O4Si

C14H26O4Si

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 30℃; for 2h; Temperature; Solvent; Reagent/catalyst;92%
methanol
67-56-1

methanol

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

methyl (1R,2R,3R,5R)-(5-chloro-2-chloromethyl-3-hydroxycyclopentyl)acetate

methyl (1R,2R,3R,5R)-(5-chloro-2-chloromethyl-3-hydroxycyclopentyl)acetate

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 7h;92%
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

7α-hydroxy-6β-hydroxymethylene-2-oxabicyclo<3.3.0>octan-3-one bistrimethylsilyl ether
118457-23-1

7α-hydroxy-6β-hydroxymethylene-2-oxabicyclo<3.3.0>octan-3-one bistrimethylsilyl ether

Conditions
ConditionsYield
at 145℃; for 1h;90%
vinyl acetate
108-05-4

vinyl acetate

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(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
57930-46-8

(1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
With ALPS at 40℃; for 24h;90%
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one
117624-93-8

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

p-Anisaldehyde dimethyl acetal
2186-92-7

p-Anisaldehyde dimethyl acetal

C16H18O5
1210039-33-0

C16H18O5

Conditions
ConditionsYield
4-methoxybenzoic acid In toluene at 120℃; for 3h; Dean-Stark apparatus;87%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one
32233-40-2

(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
67788-45-8

(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4-[(tert-butyldiphenylsilyloxy)methyl]-2H-cyclopenta[b]furan-2-one
84786-80-1

(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4-[(tert-butyldiphenylsilyloxy)methyl]-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one
39968-95-1

(3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

benzoyl chloride
98-88-4

benzoyl chloride

((3aS,4R,5S,6aR)-5-(benzoyloxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-yl)methyl benzoate

((3aS,4R,5S,6aR)-5-(benzoyloxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-yl)methyl benzoate

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

A

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one
58707-50-9, 72777-85-6, 81203-78-3, 65025-94-7

(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
117624-93-8

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one

Conditions
ConditionsYield
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
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(3aR,4S,5R,6aS)-5-p-toluenesulfoxy-4-[(p-toluenesulfoxy)methyl]hexahydrocyclopenta[b]furan-2-one
1063693-23-1

(3aR,4S,5R,6aS)-5-p-toluenesulfoxy-4-[(p-toluenesulfoxy)methyl]hexahydrocyclopenta[b]furan-2-one

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 3h;73%
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