A simple strategy for the synthesis of hydroxyethylene dipeptide isostere from D-glucose

Chakraborty, T. K. ; Azhar Hussain, K. ; Thippeswamy, D. (1995) A simple strategy for the synthesis of hydroxyethylene dipeptide isostere from D-glucose Tetrahedron, 51 (13). pp. 3873-3880. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4020(95)00109-L

Abstract

A general approach is outlined here for the synthesis of hydroxyethylene dipeptide isostere (1) starting from D-glucose which can be employed to introduce any group at P1 or P1, positions of such isosteres. A highly stereoselective synthesis of (2R̲,4S̲)-N̲-Boc-O̲-benzyl-5-amino4-hydroxy-2-methyl-6-phenylhexanoic acid methyl ester (2) is accomplished based on this strategy.

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