245054-34-6

Basic information

• Product Name: methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate
• Synonyms: methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate
• CAS NO: 245054-34-6
• Molecular Weight: 292.288
• Mol File: 245054-34-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate(245054-34-6)
• EPA Substance Registry System: methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate(245054-34-6)

Safety Data

• Hazardous Substances Data: 245054-34-6(Hazardous Substances Data)

Upstream product

• 245054-31-3 (2S,3S,4aR,8S,8aR)-methyl 8-hydroxy-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate 
• 245054-32-4 methyl (3R,4S,5R)-3-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate 
• 245054-30-2 methyl (4S,5R)-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohex-1-en-1-carboxylate 
• 183474-88-6 methyl (1S,4S,5R)-1-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohexan-1-carboxylate 
• 176798-26-8 (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 138-59-0 shikimic acid 
• 769-78-8 vinyl benzoate 
• 40983-58-2 methyl shikimate 
• 275355-06-1 (1R,5R,6R)-5-Benzoyloxy-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester 
• 245054-33-5 methyl (3R,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate 

Downstream Products

• 40983-58-2 methyl shikimate 
• 138-59-0 shikimic acid 

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 efficient transformation of quinic acid to shikimic acid derivatives

The synthesis of (-)-methyl shikimate and (-)-methyl 3-epi-shikimate and the 3-aminoshikimate derivative have been achieved via short and efficient mutes from quinic acid.