α-Glycosyl azides can be transformed into the corresponding α-glycosyl acetamides with complete retention of configuration via reduction-acylation (Staudinger ligation) reactions using specifically functionalized phosphines. The α-acetamides of per-O-benzylated-fucose, per-O-benzylated-glucose and per-O-benzylated-galactose were selectively synthesized by this process.
Selective Synthesis of Anomeric alfa-Glycosylacetamides via Intramolecular Staudinger Ligation of the alfa-Azides / A. Bianchi, A. Bernardi. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 45:10(2004), pp. 2231-2234.
Selective Synthesis of Anomeric alfa-Glycosylacetamides via Intramolecular Staudinger Ligation of the alfa-Azides
A. BianchiPrimo
;A. BernardiUltimo
2004
Abstract
α-Glycosyl azides can be transformed into the corresponding α-glycosyl acetamides with complete retention of configuration via reduction-acylation (Staudinger ligation) reactions using specifically functionalized phosphines. The α-acetamides of per-O-benzylated-fucose, per-O-benzylated-glucose and per-O-benzylated-galactose were selectively synthesized by this process.
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