950897-47-9

Upstream product

• 185810-88-2 (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester 
• 101906-39-2 Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate 
• 108-05-4 vinyl acetate 
• 185810-87-1 (4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester 
• 40983-58-2 methyl shikimate 
• 138-59-0 shikimic acid 
• 950897-46-8 (3R,4S,5R)-3,5-dihydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester 
• 950897-45-7 (3R,4S,5R)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester 

Downstream Products

• 950897-48-0 (3S,4R,5R)-3-[(1RS)-2-bromo-1-ethoxyethoxy]-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Lipase-catalyzed enantio- and regioselective transformation of 3-epi-shikimic acid derivatives as the key step for the entry of polyoxygenated carbacycles

Candida antarctica lipase B (Novozym 435)-catalyzed transesterification on methyl (±)-3,4-di-O-acetyl-5-O-(tert-butyldimethyl)silyl-3-epi-shikimate worked highly regio- and enantioselective manner. Only (3R,4S,5S)-isomer reacted with an E value over 500,

An efficient synthesis of a potential (-)-reserpine intermediate from (-)-shikimic acid of the chiral pool

A highly stereoselective route to the polysubstituted chiral octahydrobenzofuran 12, a potential synthon for the E-ring core in the (-)-reserpine synthesis, is described. The α-bromo acetal 11 was obtained from inexpensive (-)-shikimic acid (3) through a series of highly stereoselective chemical reactions (Scheme). Et3B/Bu 3SnH-Mediated intramolecular radical cyclization of 11 led to compound 12 with the required configuration.