Synthesis of glycosides of 3-deoxy-4-thiopentopyranosid-2-uloses and their reduction products: 3-Deoxy-4-thiopentopyranosides

Michael addition of common thiols to the enone system of (2S)-2-benzyloxy-2H-pyran-3(6H)-one (1) afforded the corresponding 3-deoxy-4-thiopentopyranosid-2-ulose derivatives (2-4). The reaction was highly diastereoselective, and the addition was governed by the quasiaxially disposed 2-benzyloxy subst...

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Publicado:	2002
Materias:	3-Deoxy-4-thiopentopyranosid-2-uloses 3-Deoxy-4-thiopentopyranosides Michael addition Thio sugars Addition reactions Derivatives Esters Isomers Stereochemistry Synthesis (chemical) Stereocontrols Carbohydrates 2 octyl 2 o acetyl 3 deoxy 4 s [methyl n (tert butoxycarbonyl)cysteinat 3 yl] 4 thio beta dextro threo beta dextro erythro pentapyranoside 2 octyl 3 deoxy 4 s [methyl n (tert butoxycarbonyl)cysteinat 3 yl] 4 thio beta dextro glyceropentopyranosid 2 ulose 2 octyl 3 deoxy 4 s ethyl 4 thio beta dextro glyceropentopyranosid 2 ulose 2 octyl 4 s benzyl 3 deoxy 4 thio beta dextro glyceropentopyranosid 2 ulose 2 octyl 4 s benzyl 3 deoxy 4 thio beta dextro threo pentopyranoside 2 octyl 4 s benzyl 3 deoxy 4 thio beta levo glyceropentopyranosid 2 ulose 3 deoxy 4 thiopentopyranosid 2 ulose benzyl 3 deoxy 4 s (2 propyl) 4 thio beta dextro glyceropentopyranosid 2 ulose benzyl 3 deoxy 4 s ethyl 4 thio beta dextro glyceropentopyranosid 2 ulose benzyl 4 s benzyl 3 deoxy 4 thio beta dextro glyceropentopyranosid 2 ulose cysteine derivative glycoside n (tert butoxycarbonyl)cysteine pyranosid 2 ulose pyranoside thiol derivative unclassified drug article chemical reaction enantiomer isomer optical rotation priority journal proton nuclear magnetic resonance reduction stereochemistry synthesis thin layer chromatography Carbohydrate Conformation Glycosides Magnetic Resonance Spectroscopy Pentoses Stereoisomerism Sulfhydryl Compounds Thioglycosides
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2069_Uhrig http://hdl.handle.net/20.500.12110/paper_00086215_v337_n21-23_p2069_Uhrig
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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