The Journal of Organic Chemistry

Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates

M Sakaitani, Y Ohfune

Index: Sakaitani, Masahiro; Ohfune, Yasufumi Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 870 - 876

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Citation Number: 256

Abstract

The tert-butyldimethylsilyloxycarbonyl compounds 2a and 4b can be isolated by an extractive workup and stored at ambient temperature. This group can be removed under mildly acidic conditions or by the fluoride ion treatment to give a deprotected free amine (vide infra). The silyl carbamates were used for the next reaction without further purification because partial cleavage of the silyloxycarbonyl group was accompanied by moisture or ...

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