A PRACTICAL SYNTHESIS OF (2S,3R)-3-AMINO-2-METHYLPENTANOIC ACID FROM L-ASPARTIC ACID

Authors
JEFFORD CW MCNULTY J
Citation
Cw. Jefford et J. Mcnulty, A PRACTICAL SYNTHESIS OF (2S,3R)-3-AMINO-2-METHYLPENTANOIC ACID FROM L-ASPARTIC ACID, Helvetica Chimica Acta, 77(8), 1994, pp. 2142-2146
Citations number
23
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
77
Issue
8
Year of publication
1994
Pages
2142 - 2146
Database
ISI
SICI code
0018-019X(1994)77:8<2142:APSO(A>2.0.ZU;2-I
Abstract
L-Aspartic acid by successive N-tosylation, anhydride formation, and r eduction was converted into (3S)-3-(tosylamino)butano-4-lactone (4). E lectrophilic methylation of 4, subsequent iodo-esterification and nucl eophilic methylation, followed by saponification and deprotection, gav e (2S,3R)-3-amino-2-methylpentanoic acid (2) with an ee of > 99 % in s even steps and in an overall yield of 34%.