383368-52-3

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 691-84-9 Diethyl (S)-malate 

Downstream Products

• 797050-32-9 (2S,3R)-3-benzyloxymethyl-2-benzyloxy-methoxy-1,4-butanediol 
• 383368-61-4 (2S,3S)-3-benzyloxymethyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-4-butanolide 
• 797050-37-4 (2R,3S)-2-Benzyloxymethyl-3-hydroxy-succinic acid 
• 383368-54-5 (2S,3S)-3-benzyloxymethyl-2,4-(4-methoxybenzylidenedioxy)butane-1-ol 
• 797050-33-0 (2S,3S)-3-benzyloxymethyl-2,4-(4-methoxybenzylidenedioxy)butanal 
• 797050-35-2 (2S,3S)-3-benzyloxymethyl-2-methanesulfonyloxy-4-butanolide 
• 383368-55-6 (2S,3S)-3-benzyloxymethyl-2-hydroxy-4-butanolide 
• 133435-77-5 (S)-4-((benzyloxy)methyl)dihydrofuran-2(3H)-one 
• 853270-47-0 (2S,3S)-2-(Benzyloxymethoxy)-3-(benzyloxymethyl)butane-1,4-diyl dimethanesulfonate 
• 853270-48-1 (3S,4R)-1-Benzyl-3-(benzyloxymethoxy)-4-(benzyloxymethyl)pyrrolidine 
• 1609403-89-5 cis-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride 
• 383368-53-4 (2S,3R)-3-benzyloxymethyl-1,2,4-butanetriol 

Relevant academic research and scientific papers

Process for the preparation of substituted pyrrolidine derivatives and intermediates

Two syntheses are provided; one for the preparation of (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol, and other for the preparation of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is prepared using the achiral ylide prepared from benzylamine instead of phenethylamine (Scheme 3) which provides a crystalline intermediate. The synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is achieved from (S)-diethylmalate as described in Scheme 4. A process for preparing camphor sultam is also provided.

An efficient stereoselective synthesis of (3S,4R)-4-(hydroxymethyl) pyrrolidin-3-ol from (S)-diethylmalate

A concise stereoselective synthesis of an imino sugar, (3S,4R)-4- (hydroxymethyl)pyrrolidin-3-ol from (S)-diethylmalate has been developed in five steps and in overall yield of 28%.

Stereoselective synthesis and structure of butalactin and lactone II isolated from Streptomyces species

The synthesis and stereostructure of butalactin and lactone II isolated from streptomyces species was analyzed. It was observed that butalactin exhibited moderate antibacterial activity against gram positive bacteria. It was also observed that stereoselectivity of the lactones was in the ratio 8:1. The results show that an interesting rearrangement is formed due to intramolecular double esterification of 3-oxymethyl anion.

Synthesis and absolute configuration of lactone II isolated from Streptomyces sp. Go 40/10

All four possible stereoisomers of lactone II isolated from Streptomyces sp. Go 40/10, an autoregulator, have been efficiently synthesized in a stereoselective manner starting from (S)-malic acid and sorbic acid, and the absolute configuration was determined to be 2S, 3S, 9R, 10S.