1365543-00-5

Upstream product

• 1365542-97-7 C₁₆H₂₆O₆ 
• 138-59-0 shikimic acid 
• 96-22-0 pentan-3-one 
• 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 
• 1376576-27-0 (3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate 
• 584-02-1 2-pentanol 
• 1376576-30-5 (1S,5R,6S)-methyl 7-acetyl-5-(methoxymethoxy)-7-azabicyclo[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 
• 204255-06-1 oseltamivir 
• 204255-11-8 oseltamivir phosphate 
• 196618-13-0 oseltamivir 

Relevant academic research and scientific papers

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.

A new efficient synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid

New synthesis of oseltamivir phosphate was accomplished in 9 steps with a 27% overall yield from a readily available (-)-shikimic acid. Selective ring opening reaction of ketal and azide Mitsunobu reaction for facile replacement of a hydroxyl group by the N3 group at the C-3 position of (3R,4R,5R)-ethyl 4-hydroxy-5-(methoxymethoxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 4 and at the C-4 position of (3R,4S,5R)-ethyl 4-acetamido-5-hydroxy-3-(pentan-3-yloxy) cyclohex-1-enecarboxylate 7 successfully served as the key steps.