326598-95-2

Upstream product

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

Downstream Products

• 326622-28-0 (4R,6R)-6-acetoxy-1-methyl-4-(methoxycarbonyl)cyclohexene 
• 326599-48-8 (1S,3R,4R,5S)-3-Acetoxy-5-(tert-butyl-diphenyl-silanyloxy)-4-methyl-cyclohexanecarboxylic acid methyl ester 
• 757240-15-6 (1R,5R)-5-Hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methyl ester 
• 758719-53-8 (1R,3R,4S,5R)-4-methyl-6-oxabicyclo[3.2.1]oct-7-one 
• 758719-49-2 (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde 
• 758719-44-7 (1S,3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate 
• 326599-59-1 (1R,3R,4S,5R)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxaldehyde 
• 326599-53-5 (1S,3S,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxaldehyde 
• 758719-38-9 methyl (1R,5R)-5-(tert-butyldiphenylsilyloxy)-4-methyl-3-cyclohexene-1-carboxylate 
• 758719-54-9 (1R,3R,4S,5R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-6-oxabicyclo[3.2.1]oct-7-one 
• 758719-79-8 [(1S,3R,4S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-methanol 
• 326599-58-0 [(1R,3R,4S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-methanol 
• 326599-52-4 [(1S,3S,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-methanol 

Relevant academic research and scientific papers

A convenient, large scale synthesis of trans-(+)-sobrerol

A convenient and highly efficient synthesis of optically pure trans(+)-sobrerol (1), starting from methyl 3,5-dihydroxy-4-methyl benzoate 2 in 8 steps with overall yield 26%, is reported. The key intermediate 4 is prepared in remarkably high yield by selectively esterification of 3 using lipase as catalyst. A critical step to stereoselectively inverse the configuration of 7 is realized under Mistunobu conditions.

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.