326598-95-2

Basic information

• Product Name: Cyclohexanecarboxylic acid, 3-(acetyloxy)-5-hydroxy-4-methyl-, methyl ester, (1R,3R,4S,5S)-
• CAS NO: 326598-95-2
• Molecular Formula: C11H18O5
• Molecular Weight: 230.261
• Mol File: 326598-95-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Cyclohexanecarboxylic acid, 3-(acetyloxy)-5-hydroxy-4-methyl-, methyl ester, (1R,3R,4S,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 3-(acetyloxy)-5-hydroxy-4-methyl-, methyl ester, (1R,3R,4S,5S)-(326598-95-2)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 3-(acetyloxy)-5-hydroxy-4-methyl-, methyl ester, (1R,3R,4S,5S)-(326598-95-2)

Safety Data

• Hazardous Substances Data: 326598-95-2(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 326598-92-9 all-cis-3,5-dihydroxy-4-methyl-1-(methoxycarbonyl)cyclohexane 

Downstream Products

• 34182-03-1 (R)-5-(1-hydroxy-1-methylethyl)2-methylcyclohex-2-enone 
• 607353-60-6 (4S,6R)-1-methyl-6-(4'-nitrobenzoyloxy)-4-(methoxycarbonyl)cyclohexene 
• 607353-61-7 (4S,6R)-6-hydroxy-1-methyl-4-(methoxycarbonyl)cyclohexene 
• 607353-59-3 (4S,6S)-6-hydroxy-1-methyl-4-(methoxycarbonyl)cyclohexene 
• 772-36-1 (4R,6R)-6-hydroxy-4-(1-hydroxyisopropyl)-1-methylcyclohexene 
• 38235-58-4 trans-sobrerol 
• 326599-49-9 (1S,3R,4R,5S)-5-t-butyldiphenylsilyloxy-3-hydroxy-4-methyl-1-(methoxycarbonyl)cyclohexane 
• 326599-68-2 methyl (1S,5S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-3-cyclohexene-1-carboxylate 
• 758719-37-8 1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol 

Relevant articles and documents

VITAMIN D PRESCURSORS, METHOD AND INTERMEDIATES

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Asymmetrization of all-cis-3,5-dihydroxy-1-(methoxycarbonyl)cyclohexane and of the 4-methyl and 4-ethyl substituted homologues

Enantiomerically pure mono acylated derivatives of cis,cis-3,5-dihydroxy-1-(methoxycarbonyl)cyclohexane 1, all-cis-3,5-dihydroxy-4-methyl-1-(methoxycarbonyl)cyclohexane 2 and all-cis-3,5-dihydroxy-4-ethyl-1-(methoxycarbonyl)cyclohexane 3 were obtained upon lipase catalyzed asymmetrization. PPL-catalyzed transesterification of 1 with vinyl acetate led in high yield to the (S)-monoacetate (+)-13. With substrates 2 and 3 this process was slower and gave the (R)-monoacetates (-)-14 and (-)-15; the best results were obtained with SAM II lipase. On the other hand, enantiotoposelective hydrolysis of their diacetates and especially dibutyrates gave useful results only for the 4-substituted substrates and produced the (S)-monoesters. Copyright (C) 2000 Elsevier Science Ltd.