143615-29-6

Basic information

• Product Name: (+/-)-methyl 3α-acetoxy-4α,5β-dihydroxycyclohexenoate
• CAS NO: 143615-29-6
• Molecular Weight: 230.218
• Mol File: 143615-29-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+/-)-methyl 3α-acetoxy-4α,5β-dihydroxycyclohexenoate(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-methyl 3α-acetoxy-4α,5β-dihydroxycyclohexenoate(143615-29-6)
• EPA Substance Registry System: (+/-)-methyl 3α-acetoxy-4α,5β-dihydroxycyclohexenoate(143615-29-6)

Safety Data

• Hazardous Substances Data: 143615-29-6(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 40983-58-2 methyl shikimate 
• 138-59-0 shikimic acid 
• 83604-10-8 rac-methyl 5-hydroxycyclohexa-1,3-diene-1-carboxylate 
• 563-63-3 silver(I) acetate 

Relevant articles and documents

Regioselective enzymatic acylation of methyl shikimate. Influence of acyl chain length and solvent polarity on enzyme specificity.

Candida antarctica lipase A (CAL-A) selectively catalyzes the acylation at the secondary C-4 hydroxyl group of methyl shikimate (2), which possesses three secondary hydroxyl groups, the C-3 allylic one being chemically more reactive. The effect both of the acyl group of the acylating agents and of the solvent polarity has been studied. The selectivity of CAL-A is almost complete with acyl donors that possess short chains. However, when acyl donors have longer chains, better results are obtained by C. antarctica lipase B (CAL-B).

AN IMPROVED SYNTHESIS OF (+/-)-METHYL SHIKIMATE THROUGH STEREOSELECTIVE CIS-DIHYDROXYLATION OF (+/-)-METHYL 5β-HYDROXYCYCLOHEXA-1,3-DIENOATE UNDER PREVOST'S REACTION CONDITIONS

A Prevost-type reaction under "wet" conditions upon the O-t-butyl-dimethylsilyl derivative of (+/-)-methyl 5β-hydroxycyclohexa-1,3-dienoate gives (+/-)-methyl 3α-acetoxy-4β-hydroxy-5β-t-butyldimethylsilyloxycyclohexene which may be readily deprotected to afford (+/-)-methyl shikimate in very high yield.Less selectivity is observed in a similar reaction upon the parent alcohol and when this compound is reacted under dry conditions the major product is (+/-)-methyl 4β,5β-epoxy-3β-acetoxycyclohexenoate.An analysis of Prevost reactions with exo and endo methyl 7-oxabicyclohept-5-en-2-oate is also described.