Photo amidoglycosylation of an allal azidoformate. Synthesis of beta-2-amido allopyranosides.

Kan, C; Long, C M; Paul, M; Ring, C M; Tully, S E; Rojas, C M

Kan, C; Long, C M; Paul, M; Ring, C M; Tully, S E; Rojas, C M.

Afiliación

Kan C; Department of Chemistry, Barnard College, 3009 Broadway, New York, New York 10027, USA.

Org Lett ; 3(3): 381-4, 2001 Feb 08.

Article en En | MEDLINE | ID: mdl-11428019

RESUMEN

[figure: see text] Photolysis of an allal C-3 azidoformate provoked intramolecular nitrene insertion into the glycal C=C unit and allowed direct incorporation of alcohol nucleophiles as beta-disposed substituents at C-1. The 2-amido allopyranoside products were elaborated via N-acylation and selective oxazolidinone hydrolysis, providing N-Boc-protected 2-amino sugars and simplifying stereochemical assignments. Synthesis of the potentially labile allal azidoformate was achieved via reaction of the corresponding carbonyl imidazolide with trimethylsilyl azide, facilitated by dibutyltin oxide.

Asunto(s)

Glicósidos/síntesis química; Amidas/química; Azidas/química; Conformación de Carbohidratos; Formiatos/química; Glicosilación; Fotólisis

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Glicósidos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2001 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos

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