104528-69-0

Upstream product

• 108-24-7 acetic anhydride 
• 897014-96-9 (-)-methyl 4-epi-shikimate 
• 273728-68-0 (3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester 
• 104464-05-3 (1R,4S,6S)-4-Hydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-1-(toluene-4-sulfonyl)-cyclohex-2-enecarboxylic acid methyl ester 
• 104464-08-6 (3R,4S,6S)-3,4-Dihydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester 
• 104464-14-4 methyl (3aR,7aS)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 104464-04-2 (1S,4R,8S)-8-((S)-2-Methyl-1-phenyl-propoxy)-4-(toluene-4-sulfonyl)-2-oxa-bicyclo[2.2.2]oct-5-en-3-one 
• 273728-87-3 (1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 2-benzyl ester 
• 273728-71-5 (1R,2R,3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-dicarboxylic acid 1-methyl ester 
• 273728-74-8 Acetic acid (3aR,4R,5R,6R,7aR)-6-acetoxy-1,3-dioxo-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-octahydro-isobenzofuran-5-yl ester 
• 273728-83-9 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3aR,4R,5R,6R,7aR)-5,6-dihydroxy-1,3-dioxo-octahydro-isobenzofuran-4-yloxy)-tetrahydro-pyran-3-yl ester 
• 21967-35-1 (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 
• 104464-18-8 (3aR,7R,7aS)-methyl 7-hydroxy-2,2-dimethyl-3a,4,7,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate 

Relevant academic research and scientific papers

Asymmetric synthesis of (-)-4-epi-shikimic acid

The major cycloadduct, arising from the Diels-Alder reaction of maleic anhydride and (1E)-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)buta- 1,3-diene, is converted into methyl 3-O-(β-D-glucopyranosyl)-4-epi-shikimate and into (-)-4-epi-shikimic acid in overall yields of 20 and 17% (based on the diene). (C) 2000 Elsevier Science Ltd.

Highly Stereocontrolled Synyhesis of Some Trioxygenated Cyclohexenes: An Asymmetric Total Synthesis of (-)-Methyl Triacetyl-4-epishikimate

Polyfunctional bicyclic lactone (-)-1 serves as a chiron for preparation of 3,4,6-trioxygenated cyclohexene (-)-5a in 56.6percent overall yield and for synthesis of (-)-methyl triacetyl-4-epishikimate, (-)-12, in 14 steps and in 23.4percent overall yield.