288269-07-8

Basic information

• Product Name: (3aR,6S,6aR)-2,2-Dimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-one
• Synonyms: (3aR,6S,6aR)-2,2-Dimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-one
• CAS NO: 288269-07-8
• Molecular Weight: 290.359
• Mol File: 288269-07-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3aR,6S,6aR)-2,2-Dimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,6S,6aR)-2,2-Dimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-one(288269-07-8)
• EPA Substance Registry System: (3aR,6S,6aR)-2,2-Dimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-one(288269-07-8)

Safety Data

• Hazardous Substances Data: 288269-07-8(Hazardous Substances Data)

Upstream product

• 288269-03-4 (1S,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(1-methyl-1-phenyl-ethoxy)-cyclopentane-1,2-diol 
• 288269-04-5 tert-Butyl-[(3aR,4R,6S,6aR)-2,2-dimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-yloxy]-dimethyl-silane 
• 288269-02-3 (-)-cis-1-(t-butyldimethyl silyloxy)-4-cumyloxy-2-cyclopentene 
• 258834-28-5 (+)-(cis-1,4)-4-Cumyloxycyclopent-2-en-1-ol 
• 288269-06-7 (3aS,4R,6S,6aR)-2,2-Dimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-ol 

Downstream Products

• 115509-13-2 (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 

Relevant articles and documents

Chiral preparation of polyoxygenated cyclopentanoids

A series of polyoxygenated cyclopentanoids, including 2,2-dimethyl- 3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one, has been prepared in both enantiomeric forms from cyclopentadiene by employing lipase-mediated kinetic resolution as the key step. Thus, cyclopentadiene is first transformed into racemic cis-4-cumyloxycyclopent-2-en-1-ol which is resolved under transesterification conditions in the presence of lipase PS. After transformation into the corresponding tert-butyldimethylsilyl (TBS) ethers, each of the enantiomers is cis-dihydroxylated diastereoselectively from the less hindered face which is transformed into the 2,3-O-isopropylidene-1,4-di- O-protected (trans-1,2:cis-2,3:trans-3,4)-1,2,3,4-cyclopentanetetraol. Selective removal of the 1,4-protecting group gives the corresponding 2,3,4- O-protected cyclopentanols which are further transformed into the 2,3,4-O- protected cyclopentanones on oxidation without suffering β-elimination. Exposure of the cyclopentanones to warm acetic acid allows β-elimination to give rise to the dehydration product 2,2,-dimethyl-3a,6a-dihydro-4H- cyclopenta[d][1,3]dioxol-4-one having the corresponding chirality without losing their original chiral integrity.