131690-27-2

Upstream product

• 5469-16-9 4-Hydroxy-dihydro-furan-2-on 
• 540-88-5 acetic acid tert-butyl ester 
• 693-04-9 butyl magnesium bromide 
• 98-88-4 benzoyl chloride 
• 677-22-5 tert-butylmagnesium chloride 
• 1067638-08-7 C₁₀H₁₈O₅ 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 7440-66-6 zinc 

Downstream Products

• 131666-49-4 (2S,4R)-6-tert-butoxy-2,4-dihydroxy-6-oxohexyl benzoate 

Relevant academic research and scientific papers

Efficient synthesis of (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative as a chiral side chain of statins

Efficient synthesis of tert-butyl [(3R,5S)-6-hydroxy-methyl-2,2-dimethyl-1, 3-dioxan-4-yl]acetate (1) has been accomplished. Unprecedented hydration of 3 in the presence of lithium chloride provided 4a,b, the primary hydroxyl group of which reacted with pivaloyl- and 1-naphthoyl chloride, respectively, in pyri-dine to give 7a or 7d in improved selectivity. Diastereoselective reduction of 7a and protection-deprotection sequence provided 1.

PROCESS FOR PREPARING OPTICALLY ACTIVE 2- 6-(HYDROXY-METHYL)-1,3-DIOXAN-4-YL]ACETIC ACID DERIVATIVES

The present invention is to provide a production technology by which an optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivative, which are of value as pharmaceutical intermediates, can be produced from inexpensive and readily available starting materials without using any extraordinary equipment such as an ultra-low-temperature reactor. The present invention is a production process of an optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivative ???which comprises reacting an enolate, prepared by permitting a base or a 0-valent metal to act on an acetic acid ester derivative with (S)-β-hydroxy-γ-butyrolactone at a temperature not lower than -30°C to give a dihydroxyoxohexanoic acid derivative, ???treating the same with an acylating agent in the presence of a base to produce a dihydroxyoxohexanoic acid monoacyl derivative, ???reducing this compound with a microorganism to produce a trihydroxyhexanoic acid monoacyl derivative, ???treating this compound with an acetal-forming reagent in the presence of an acid catalyst to produce an acyloxymethyldioxanylacetic acid derivative, and ???finally, subjecting this compound to solvolysis in the presence of a base.

Process for the production of 3,5,6-trihydroxyhexanoic acid derivative

A compound of a 3,5,6-trihydroxyhexanoic acid derivative of the formula: STR1 wherein P1 and P2 are independently hydrogen atoms or hydroxy-protecting groups, or together form a ring, and R is an alkyl group is effectively prepared by a process comprising steps of: reacting a butyronitrile derivative of the formula: STR2 wherein P1 and P2 are the same as defined above with an α-haloacetate of the formula: wherein X is a halogen atom, and R is the same as defined above in the presence of a metallic catalyst selected from the group consisting zinc and zinc-copper to form a keto acid derivative of the formula: STR3 wherein P1, P2 and R are the same as defined above, and then reducing the obtained keto-acid derivative of the formula (IV).