6H-Cyclopenta[b]furan-6-one, hexahydro-3a,6a-dihydroxy-, (3aR,6aR)-rel- (9CI)

Base Information

• Chemical Name: 6H-Cyclopenta[b]furan-6-one, hexahydro-3a,6a-dihydroxy-, (3aR,6aR)-rel- (9CI)
• CAS No.: 587875-10-3
• Molecular Formula: C7H10O4
• Molecular Weight: 158.15
• Mol file: 587875-10-3.mol

Synonyms:6H-Cyclopenta[b]furan-6-one, hexahydro-3a,6a-dihydroxy-, (3aR,6aR)-rel- (9CI)

Chemical Property of 6H-Cyclopenta[b]furan-6-one, hexahydro-3a,6a-dihydroxy-, (3aR,6aR)-rel- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6H-Cyclopenta[b]furan-6-one, hexahydro-3a,6a-dihydroxy-, (3aR,6aR)-rel- (9CI)

There total 9 articles about 6H-Cyclopenta[b]furan-6-one, hexahydro-3a,6a-dihydroxy-, (3aR,6aR)-rel- (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

3-(2-hydroxyethyl)-1,2-cyclopentanedione → 1,5-dihydroxy-2-oxabicyclo[3.3.0]octane-8-one (587875-10-3) + (R)-3-(3-hydroxy-2-oxotetrahydrofuran-3-yl)propanoic acid

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; (+)-Weinsaeure-diethylester; In decane; dichloromethane; at -20 ℃; for 68h;

DOI:10.1016/S0957-4166(03)00452-X

Reference yield: 25.0%

2-hydroxy-3-(2-hydroxyxyethyl)cyclopent-2-en-1-one (303183-80-4) → 1,5-dihydroxy-2-oxabicyclo[3.3.0]octane-8-one (587875-10-3)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; (+)-Weinsaeure-diethylester; In dichloromethane; at -20 ℃; for 42h;

DOI:10.1016/S0957-4166(02)00589-X

Reference yield: 18.0%

methanol (67-56-1) + 2-hydroxy-3-(2-tert-butyldimethylsilyloxyethyl)cyclopent-2-en-1-one (303183-81-5) → 1,7-dioxaspiro[4.4]nonane-2,6-dione + 3-((R)-3-Hydroxy-2-oxo-tetrahydro-furan-3-yl)-propionic acid methyl ester + 3-((S)-3-Hydroxy-2-oxo-tetrahydro-furan-3-yl)-propionic acid methyl ester + 1,5-dihydroxy-2-oxabicyclo[3.3.0]octane-8-one (587875-10-3)

Guidance literature:

2-hydroxy-3-(2-tert-butyldimethylsilyloxyethyl)cyclopent-2-en-1-one; With titanium(IV) isopropylate; tert.-butylhydroperoxide; (+)-Weinsaeure-diethylester; In dichloromethane; at -20 ℃; for 42h;

methanol; With citric acid; In dichloromethane; Further byproducts given;

DOI:10.1016/S0040-4039(00)01106-0

upstream raw materials:

methanol

2-hydroxy-3-(2-tert-butyldimethylsilyloxyethyl)cyclopent-2-en-1-one

2-hydroxy-3-(2-hydroxyxyethyl)cyclopent-2-en-1-one

2-cyclopent-2-enyl-ethanol