1376576-27-0

Basic information

• Product Name: (3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate
• Synonyms: (3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate
• CAS NO: 1376576-27-0
• Molecular Weight: 257.246
• Mol File: 1376576-27-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate(1376576-27-0)
• EPA Substance Registry System: (3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate(1376576-27-0)

Safety Data

• Hazardous Substances Data: 1376576-27-0(Hazardous Substances Data)

Upstream product

• 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 

Downstream Products

• 1149345-89-0 ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate 
• 1132659-99-4 (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1365543-00-5 C₁₈H₃₁NO₆ 
• 196618-13-0 oseltamivir 
• 204255-06-1 oseltamivir 

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.