Synthesis of glycyl-(S)-5-hydroxynorvaline

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Abstract

The dipeptide glycyl-( S )-5-hydroxynorvaline was obtained from 1- tert -butyl 5-methyl N -Boc-glycyl-( S )-glutamate as a result of saponification and subsequent reduction of the activated 5-carboxyl group with sodium borohydride followed by removal of the N -Boc and OBu t protecting groups by refluxing in a dioxane-water mixture. Using the example of the synthesis of ( S )-5-hydroxynorvaline, it has been shown that the used sequence of chemical transformations is not accompanied by racemization.

About the authors

E. N. Chulakov

Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

Email: chulakov@ios.uran.ru

A. A. Tumashov

Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

D. A. Gruzdev

Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

G. L. Levit

Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

V. P. Krasnov

Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

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