13398-40-8

Basic information

• Product Name: (2R,3R)-threo-β-methylmalic acid
• Synonyms: (2R,3R)-threo-β-methylmalic acid
• CAS NO: 13398-40-8
• Molecular Weight: 148.116
• Mol File: 13398-40-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2R,3R)-threo-β-methylmalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-threo-β-methylmalic acid(13398-40-8)
• EPA Substance Registry System: (2R,3R)-threo-β-methylmalic acid(13398-40-8)

Safety Data

• Hazardous Substances Data: 13398-40-8(Hazardous Substances Data)

Upstream product

• 63921-06-2 3-methyl-2-oxo-butane-1,4-dioic acid dimethyl ester 
• 93504-92-8 2-hydroxy-3-methylbutanedioic acid diethyl ester 
• 759-65-9 diethyl oxalpropionate 
• 642-92-2 D,L-threo-β-methylaspartic acid 
• 113564-09-3 (E,2R^*,3S^*)-3-hydroxy-2-methyl-4-hexenoic acid 
• 874646-35-2 diisopropyl (2S,3R)-2-methyl-3-hydroxybutanedioate 
• 86562-29-0 (2R,3R)-(-)-threo-3-methylaspartic acid 
• 100806-42-6 (E)-(2S,3S)-3-Hydroxy-2-methyl-hex-4-enoic acid 

Downstream Products

• 2216-54-8 L-menthylamine 
• 20706-69-8 (1S,3S,4R)-menthylamine 
• 86535-06-0 (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate 
• 86535-10-6 (2S,3S)-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 
• 86535-14-0 (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol 
• 86535-08-2 (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether 
• 86535-07-1 (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 
• 83997-86-8 serricornin acetate <(4S,6S,7S)-4,6-dimethyl-7-acetoxy-3-nonanone> 
• 149-31-5 (2S,3S)-2-methylpentane-1,3-diol 
• 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 
• 72598-35-7 (-)-serricornin 

Relevant articles and documents

N-HYDROXYAMIDE DERIVATIVES AND USE THEREOF

The present invention is related to N-hydroxyamide derivatives of Formula (I) and use thereof, in particular for the treatment and/or prophylaxis of autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, cancer, respiratory diseases and fibrosis, including multiple sclerosis, arthritis, emphysema, chronic obstructive pulmonary disease, liver and pulmonary fibrosis.

Synthesis of erythro-2-Hydroxy-3-methylbutane-1,4-dioic Acid

Reduction of ethyl 3-methyl-2-oxobutane-1,4-dioate (3) with sodium borohydride furnishes a 6:1 mixture of ethyl erythro-2-hydroxy-3-methylbutane-1,4-dioate (8) and ethyl threo-2-hydroxy-3-methylbutane-1,4-dioate (18).Hydrolysis of this mixture with aq. hydrochloric acid gives a mixture of acids from which pure erythro-2-hydroxy-3-methylbutane-1,4-dioic acid (4) has been isolated.The stereochemistry of 4 has been establishrd by PMR and by transforming it to the anhydride, erythro-dihydro-3-acetyloxy-4-methyl-2,5-furandione (26).

SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN

The absolute stereochemistry of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone) was established as 4S, 6S, 7S by synthesizing both (4S, 6S, 7S)-isomer and its antipode.Only the natural enantiomer was bioactive.by