title: Photo amidoglycosylation of an allal azidoformate. Synthesis of beta-2-amido allopyranosides.
abstract: [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.
authors: Department of Chemistry, Barnard College, 3009 Broadway, New York, New York 10027, USA.
authors: C
authors: C
authors: Kan
authors: C M
authors: CM
authors: Long
authors: M
authors: M
authors: Paul
authors: C M
authors: CM
authors: Ring
authors: S E
authors: SE
authors: Tully
authors: C M
authors: CM
authors: Rojas
mesh_terms: D000577:Amides / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002236:Carbohydrate Conformation; D005561:Formates / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D010782:Photolysis
chemical_list: D000577:Amides; D001386:Azides; D005561:Formates; D006027:Glycosides