13398-41-9

Basic information

• Product Name: erythro-2-hydroxy-3-methylbutane-1,4-dioic acid
• CAS NO: 13398-41-9
• Molecular Weight: 148.116
• Mol File: 13398-41-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: erythro-2-hydroxy-3-methylbutane-1,4-dioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: erythro-2-hydroxy-3-methylbutane-1,4-dioic acid(13398-41-9)
• EPA Substance Registry System: erythro-2-hydroxy-3-methylbutane-1,4-dioic acid(13398-41-9)

Safety Data

• Hazardous Substances Data: 13398-41-9(Hazardous Substances Data)

Upstream product

• 642-92-2 D,L-threo-β-methylaspartic acid 
• 759-65-9 diethyl oxalpropionate 
• 63921-06-2 3-methyl-2-oxo-butane-1,4-dioic acid dimethyl ester 
• 93504-92-8 2-hydroxy-3-methylbutanedioic acid diethyl ester 
• 113564-09-3 (E,2R^*,3S^*)-3-hydroxy-2-methyl-4-hexenoic acid 
• 100806-42-6 (E)-(2S,3S)-3-Hydroxy-2-methyl-hex-4-enoic acid 
• 874646-33-0 diisopropyl (2R,3S)-2-methyl-3-hydroxybutanedioate 
• 6061-13-8 (2S,3S)-3-methylaspartic acid 

Downstream Products

• 72522-40-8 (4RS,6R,7R)-threo-serricornin 
• 78433-60-0 (2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-methylpentyl 4-methylbenzenesulfonate 
• 78433-58-6 ((1R,2R)-3-Benzyloxy-1-ethyl-2-methyl-propoxy)-tert-butyl-dimethyl-silane 
• 86562-36-9 (2R,3R)-threo-2-methylpentane-1,3-diol 3-THP ether 1-tosylate 
• 86535-18-4 2-methyl-3-pentanol (S)-(-)-MTPA ester 
• 86535-19-5 2-methyl-3-pentanol (R)-(+)-MTPA ester 
• 86535-17-3 (2R,3R)-threo-2-methylpentane-1,3-diol 1-tosylate 
• 86562-34-7 (2R,3R)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether 
• 83997-86-8 serricornin acetate <(4S,6S,7S)-4,6-dimethyl-7-acetoxy-3-nonanone> 
• 78433-55-3 (2S,3R)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate 
• 78479-16-0 (2S,3R)-threo-3-methylbutane-1,2,4-triol 4-benzyl ether 
• 78479-15-9 (2S,3R)-threo-3-methylbutane-1,2,4-triol 1,2-acetonide 4-benzyl ether 
• 82335-98-6 serricornin acetate <(4S,6R,7R)-4,6-dimethyl-7-acetoxy-3-nonanone> 
• 72485-37-1 (4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone 

Relevant articles and documents

DETERMINATION OF THE ABSOLUTE CONFIGURATION AT C-6 AND C-7 SERRICORNIN (4,6-DIMETHYL-7-HYDROXY-3-NONANONE), THE SEX PHEROMONE OF THE CIGARETTE BEETLE

The absolute configuration at C-6 and C-7 of serricornin was established as (6S, 7S) by synthesizing its (6R, 7S)-erythro and (6R, 7R)-threo isomers.

On the Stereochemistry of E'- and E''-Reactions

The decarboxylative E'-dehydration of β,γ-unsaturated δ-hydroxy acids with DMF-dineopentylacetal shows SYN-faciality irrespective of whether the conformation of the hydroxy group relative to the double bond axis is anticlinal or synclinal.

The Use of Microorganisms in Organic Synthesis. II. Microbiological Asymmetric Reduction of 2-Methyl-3-oxosuccinates

In order to synthesize four optically active methyl 2-methylmalates (10-13), microbiological asymmetric reduction of the corresponding dimethyl 2-methyl-3-oxosuccinate (9) was carried out.The β-keto diester 9 was found to be reduced by fermenting baker's yeast (Saccharomyces cerevisiae) and Candida albicans to afford a mixture of the (2R,3R)-isomer 10 and the (2S,3R)-isomer 11.Although the optical purity of 10 produced by Candida albicans was reasonably high (95percent e.e.), optical yields of other products were unexpectedly low.However, identification of the four possible isomers 14-17 was found to be easily carried out by means of nuclear magnetic resonance spectroscopy.Keywords - α-methyl-β-keto ester; methylmalate; asymmetric reduction; microbiological reduction; yeast; methyl 2-methylmalate