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Stereoselective synthesis of fully protected (2S,4S,6S)-2-amino-6-hydroxy-4-methyl-8-oxodecanoic acid (AHMOD).

Journal of peptide science : an official publication of the European Peptide Society (2012-01-18)
Wei Zhang, Xiangpeng Li, Ning Ding, Yingxia Li
ABSTRACT

The stereocontrolled synthesis of fully protected (2S,4S,6S)-2-amino-6-hydroxy-4-methyl-8-oxodecanoic acid was accomplished using a glutamate derivative as starting material. The key steps of this stereochemical synthetic pathway involved an Evans asymmetric alkylation, a Sharpless asymmetric epoxidation, and a Grignard reaction.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Decanoic acid, natural, ≥98%, FCC, FG
Supelco
Decanoic acid, analytical standard
Sigma-Aldrich
Decanoic acid, ≥98.0%
Sigma-Aldrich
Decanoic acid, ≥99.5%, FCC, FG
Sigma-Aldrich
Sodium decanoate, ≥98%