171963-38-5

Upstream product

• 78844-86-7 methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate 
• 186581-53-3 diazomethane 
• 171963-37-4 3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid 
• 84806-48-4 methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate 
• 1376576-18-9 ethyl (4R)-4-((2S,3R)-3-(hydroxymethyl)oxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate 
• 1376576-15-6 ethyl (4R)-4-((2S,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate 
• 1376576-12-3 ethyl (4R)-4-((2S,3R)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-4-hydroxy-2-methylenebutanoate 
• 1376575-69-7 (1R,5R,6S)-methyl 5-(methoxymethoxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylate 
• 1376576-24-7 (4R)-methyl 4-(methoxymethoxy)-2-methylene-4-((2S,3R)-3-vinyloxiran-2-yl)butanoate 
• 1376576-21-4 (R)-methyl 4-((2S,3R)-3-ethynyloxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate 
• 2922-42-1 (-)-3-dehydroshikimic acid 
• 77-95-2 D-(-)-quinic acid 
• 179738-33-1 Benzoic acid (1S,2S,6R)-2-bromo-6-hydroxy-4-methoxycarbonyl-cyclohex-3-enyl ester 
• 179738-32-0 Benzoic acid (1S,2S,6R)-2-chloro-6-hydroxy-4-methoxycarbonyl-cyclohex-3-enyl ester 

Downstream Products

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

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.

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.

Conversion of (-)-3-dehydroshikimic acid into derivatives of the (+)-enantiomer

(-)-3-DHS (1), a compound available in large quantity through "engineering" of the shikimic acid pathway, has been converted over eight steps into the methyl ester, ent-2, of the (+)-enantiomer. Methyl (+)-shikimate (15) and its C-3 epimer (ent-5) have al

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

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.

Synthesis of (3R)- and (3S)-fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1- carboxylic acids: The (3R)- and (3S)-fluoro analogues of (-)-shikimic acid

(3R)-and (3S)-Fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids (the (3R)- and (3S)-fluoro analogues of (-)-shikimic acid) have been synthesised from (-)-shikimic acid via an intermediate epoxide (a fungal metabolite from Chalara microspora) that

The shikimate pathway. Part 9. Halogenation at C-3 of the shikimate nucleus

The use of (-)-shikimic acid as starting material in the syntheses of a series of C-3 halogenated derivatives including the analogous 3α- and 3β-fluoro and 3β-chloro acids is described together with the first stereospecific synthesis of (-)-3-epi-shikimic acid directly from the parent acid.