175408-85-2

Upstream product

• 3282-30-2 pivaloyl chloride 
• 168776-29-2 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-5,6-di-O-pivaloyl-α-D-allofuranose 

Downstream Products

• 175408-91-0 2,2-Dimethyl-propionic acid (1R,2R,3S)-3-benzyloxy-1-(2,2-dimethyl-propionyloxymethyl)-2-methoxymethoxy-3-methyl-nonyl ester 
• 175408-88-5 2,2-Dimethyl-propionic acid (1R,2R,3R)-3-benzyloxy-1-(2,2-dimethyl-propionyloxymethyl)-3-methyl-4-oxo-2-trimethylsilanyloxy-butyl ester 
• 175408-93-2 2,2-Dimethyl-propionic acid (2R,3R,4S)-4-benzyloxy-2-hydroxy-3-methoxymethoxy-4-methyl-decyl ester 
• 175408-94-3 (2R,3R,4S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3-methoxymethoxy-4-methyl-decan-2-ol 
• 175408-92-1 (2R,3R,4S)-4-Benzyloxy-3-methoxymethoxy-4-methyl-decane-1,2-diol 
• 168776-32-7 (2R,3R,4S,5Z)-4-(benzyloxy)-3-(methoxymethoxy)-4-methyl-1,2-bis(pivaloyloxy)-5-decene 
• 168776-31-6 (2R,3R,4R)-2-(benzyloxy)-3-(methoxymethoxy)-2-methyl-4,5-bis(pivaloyloxy)pentanal 
• 175408-87-4 2,2-Dimethyl-propionic acid (1R,2R,3R)-3-benzyloxy-1-(2,2-dimethyl-propionyloxymethyl)-2-hydroxy-3-methyl-4-oxo-butyl ester 

Relevant academic research and scientific papers

Preparation of C-3,5-acyl furanoses via highly selective intramolecular acyl migration

A practical synthesis of C-3,5-acyl furanose via a base-catalyzed, highly selective intramolecular acyl migration in alcohol solvents is reported.

Total synthesis of natural PI-091, a new platelet aggregation inhibitor of microbial origin

The total synthesis of a new platelet aggregation-inhibiting γ-lactam PI-091 (1) gave a 1:1 diastereomeric mixture at the γ-ketal carbon. The high-yielding aldol reaction of an appropriately protected 1,3,4-trihydroxy-4-methyldecan-2-one 42, prepared from D-glucose, with the kinetically generated enolate of 3-methyl-2-butanone provided 43. The resulting diastereomeric mixture of the aldol adduct 43 was converted to a 2,4-alkylated furan 45 via an intramolecular ketalization followed by dehydration. The addition of a singlet oxygen to the α-trimethylsilylated furan 48 derived from 45 under photochemical conditions efficiently provided an α,γ-dialkylated γ-hydroxy γ-lactone 47. The transformation of methyl ketal 52 prepared from 47 into γ-hydroxy γ-lactam 53 was achieved by exposure to liquid ammonia in MeOH. The total synthesis of 1 was achieved from 52 through the Dess-Martin periodinane oxidation of the secondary hydroxy group in the side chain. The present total synthesis revealed that the stereogenic carbon center in the side chain in natural 1 is S.