236751-52-3

Basic information

• Product Name: 2(S)-Amino-3(S),4(S)-dihydroxypentanedioic acid
• Synonyms: 4S)-DHGA; 3(S),4(S)-Dihydroxy-L-glutamic acid
• CAS NO: 236751-52-3
• Molecular Formula: C₅H₉NO₆
• Molecular Weight: 179.13058
• Mol File: 236751-52-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2(S)-Amino-3(S),4(S)-dihydroxypentanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2(S)-Amino-3(S),4(S)-dihydroxypentanedioic acid(236751-52-3)
• EPA Substance Registry System: 2(S)-Amino-3(S),4(S)-dihydroxypentanedioic acid(236751-52-3)

Safety Data

• Hazardous Substances Data: 236751-52-3(Hazardous Substances Data)

Upstream product

• 236751-84-1 (1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one 
• 100-51-6 benzyl alcohol 
• 773143-72-9 (3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile 
• 254441-94-6 (3R,4R,5S)-3,4-O-isopropylidene-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 98-79-3 L-Pyroglutamic acid 
• 254441-93-5 (3R,4R,5R)-3,4-O-isopropylidene-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 500759-36-4 (3S,4R,5S)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 500759-35-3 (3S,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 370839-88-6 (3R,4S,5S)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 370839-89-7 (3R,4S,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 236751-80-7 benzyl 2,3-aziridino-N-(benzyloxycarbonyl)-2,3-dideoxy-β-D-lyxofuranuronate 
• 773143-70-7 Acetic acid (3S,4S)-4-acetoxy-2-cyano-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-3-yl ester 
• 773143-71-8 (3aS,4R,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile 
• 570429-68-4 (S)-5-Oxo-pyrrolidine-2-carboxylic acid 2-(2-methyl-oxiranyl)-ethyl ester 

Relevant articles and documents

First enantiospecific synthesis of a 3,4-dihydroxy-L-glutamic acid [(3S,4S)-DHGA], a new mGluR1 agonist

The first synthesis of one of the 4 possible stereoisomers of 3,4- dihydroxy-L-glutamic acid ((3S,4S)-DHGA 3), a natural product of unknown configuration, is described. The synthesis is based on the Lewis acid catalyzed reaction of benzyl alcohol with a D

Synthesis and reactions of a novel 3,4-didehydropyroglutamate derivative

Some reactions such as catalytic hydrogenation, Diels-Alder reaction, cyclopropanation, dihydroxylation, and Michael addition of a novel 3,4-didehydropyroglutamate derivative, in which the carboxylic group is protected as an ABO ester, are examined and found to take place in a stereospecific manner giving 3- and/or 4-substituted pyroglutamate derivatives without loss of enantiomeric purity at the α-position.

A concise diastereoselective synthesis of (2S,3S,4R)-3,4-dihydroxyglutamic acid

A concise diastereoselective synthesis of (2S,3S,4R)-3,4-dihydroxyglutamic acid, one of eight possible stereoisomers of 3,4-dihydroxyglutamic acids, is described. The key reaction in this synthesis is stereoselective cyanation of an optically active N-acyliminium intermediate derived from L-tartaric acid with tributyltin cyanide.