Tetrahedron

Allylic protection of thiols and cysteine: I: The allyloxycarbonylaminomethyl group

AM Kimbonguila, A Merzouk, F Guibé, A Loffet

Index: Kimbonguila, Andre Malanda; Merzouk, Ahmed; Guibe, Francois; Loffet, Albert Tetrahedron, 1999 , vol. 55, # 22 p. 6931 - 6944

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Citation Number: 23

Abstract

S-allyloxycarbonylaminomethyl derivatives of thiols in general and cysteine in particular are readily deprotected by palladium catalysed hydrostannolysis with tributyltin hydride in the presence of acetic acid. They are perfectly stable in the basic conditions (piperidine/DMF) of Fmoc group removal but tend to decompose, albeit slowly, in the acidic conditions (TFA CH 2Cl 2) of t-Bu and Boc groups removal.

~98%

~30%

~73%

~68%

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