Studies of the stereoselective reduction of 2-hydroxyimino-hexopyranosides: LiBH4-Me3SiCl, a mild reducing agent of oximes to amines

Autor: Anna Banaszek, Wojciech Karpiesiuk
Rok vydání: 1994
Předmět:
Zdroj: Carbohydrate Research. 251:233-242
ISSN: 0008-6215
DOI: 10.1016/0008-6215(94)84288-4
Popis: Reduction of the title compounds of types 1 and 2 under mild conditions using LiBH 4 -Me 3 SiCl species, followed by acetylation, yielded the corresponding 2-amino sugars of α- d - gluco ( 5 ) and β- d - manno ( 6 ) configuration, respectively, with full stereoselectivity. Analogousy, the β- d - lyxo isomer of type 4 afforded the β- d -talosamine 9 exclusively. The stereochemical outcome of the reduction of oximes of type 3 is controlled by the configuration of the substrate and the chemical features of the C-1-C-4 substituents, leading to talo ( 8 ) and/or galacto ( 7 ) isomers.
Databáze: OpenAIRE