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2499405

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1999
protection, deprotection
protection, deprotection
O 0345
Allylic Protection of Thiols and Cysteine. Part 1. The Allyloxycar38 - 079 bonylaminomethyl Group. — The title S-Allocam protecting group is
studied on thiol derivatives (I) and cysteine derivatives (III). It is found that
under palladium-catalyzed hydrostannolysis in the presence of AcOH ready
deprotection takes place. Since isolation of the thiols from the reaction mixtures
is difficult, they are converted into the corresponding disulfides (II) or (IV).
Rearranged allyl thioethers (V) are obtained from the Allocam derivatives (III)
in the presence of Pd(PPh3 )4 . Transacylations are also successfully carried out
with carboxylic anhydrides or chloroformates. The Allocam derivatives are perfectly stable in basic conditions of Fmoc group removal (piperidine/DMF), but
tend to decompose in the acidic t-Bu and Boc group removal (TFA/CH2 Cl2 ).
— (MALANDA KIMBONGUILA, ANDRE; MERZOUK, AHMED; GUIBE,
FRANCOIS; LOFFER, ALBERT; Tetrahedron 55 (1999) 22, 6931-6944; Lab.
React. Org. Sel., Inst. Chim. Mol. Orsay, CNRS, Univ. Paris-Sud, F-91405
Orsay, Fr.; EN)
1
1999
protection, deprotection
2
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