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β-Trimethylsilylethanesulfonyl chloride (SES-Cl): A new reagent for protection of amines

✍ Scribed by Steven M Weinreb; Donald M Demko; Thomas A Lessen; James P Demers


Book ID
104218540
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
181 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis


The title compound, easily prepared in two steps from vinyltrimethylsilane, is a useful reagent for the protection of primary and secondary amines as their sulfonamides, which are cleaved by fluoride ion.

Sulfonamides are among the most stable of amine protecting groups.' However,


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A new reagent --4-nitro-l-H-pyrazole-l-[N, N'-bis(ten-butoxycarbonyl)]cmboxamidine --has been develolxd to effect the rapid a~l efficient synthesis of I~(~)-pmtected guanidin~ from and secendm3, amines. The reagent is a more eleclrophilic, sad comfy more derivative of the literature reagent l-H-pyra