171963-38-5

Basic information

• Product Name: methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate
• Synonyms: methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate
• CAS NO: 171963-38-5
• Molecular Weight: 188.18
• Mol File: 171963-38-5.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate(171963-38-5)
• EPA Substance Registry System: methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate(171963-38-5)

Safety Data

• Hazardous Substances Data: 171963-38-5(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 171963-37-4 3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid 
• 1376576-21-4 (R)-methyl 4-((2S,3R)-3-ethynyloxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate 
• 1376576-24-7 (4R)-methyl 4-(methoxymethoxy)-2-methylene-4-((2S,3R)-3-vinyloxiran-2-yl)butanoate 
• 1376575-69-7 (1R,5R,6S)-methyl 5-(methoxymethoxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylate 
• 1376576-12-3 ethyl (4R)-4-((2S,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-4-hydroxy-2-methylenebutanoate 
• 1376576-15-6 ethyl (4R)-4-((2S,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate 
• 1376576-18-9 ethyl (4R)-4-((2S,3R)-3-(hydroxymethyl)oxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate 
• 2922-42-1 (-)-3-dehydroshikimic acid 
• 77-95-2 D-(-)-quinic acid 
• 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 
• 78844-86-7 methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate 
• 84806-48-4 methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate 
• 138-59-0 shikimic acid 

Downstream Products

• 141781-68-2 (+)-Methyl shikimate 
• 171963-37-4 3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF OSELTAMIVIR AND METHYL 3-EPI-SHIKIMATE

The present invention discloses high yielding enantioselective process for synthesis of Oseltamivir from readily available starting material, cis-1,4-butene diol. The process features incorporation of chirality using sharpless asymmetric epoxidation (AE) and diastereoselective Barbier allylation and construction of cyclohexene carboxylic acid ester core through a ring closing metathesis (RCM) reaction. Further also disclosed herein is synthesis of (?)-methyl 3-epi-shikimate.

Synthesis of the anti-influenza agent (-)-oseltamivir free base and (-)-methyl 3-epi-shikimate

A new enantioselective synthesis of the anti-influenza agent (-)-oseltamivir free base (7.1% overall yield; 98% ee) and (-)-methyl 3-epi-shikimate (16% overall yield; 98% ee) has been described from readily available raw materials. Sharpless asymmetric epoxidation and diastereoselective Barbier allylation of an aldehyde are the key reactions employed in the incorporation of chirality, while the cyclohexene carboxylic ester core was constructed through a ring closing metathesis reaction.

Efficient synthesis of (-)-methyl 3-epi-shikimate and methyl 3-epi-quinate by one-pot selective protection of trans-1,2-diols

trans-1,2-Diol protections of shikimic and quinic acids have been achieved by in situ formation of the protecting group (2,2,3,3-tetramethoxybutane). The synthetic utility of the protected derivatives is demonstrated by the preparation of (-)-methyl 3-epi