A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor

Competitive glycosylation experiments with a galactofuranosyl trichloroacetimidate donor were performed with glucosamine acceptors having a free 4-OH group and carrying different protecting groups at N-2, O-3, and O-6. The most reactive acceptor is the N-dimethylmaleimido 3,6-di-O-benzylated derivat...

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Detalles Bibliográficos
Autor principal: Stortz, Carlos Arturo
Publicado: 2006
Materias:
Competitive glycosylations
DFT
Galactofuranosyl donor
Glucosamine acceptors
N-Dimethylmaleoyl group
Conformations
Glucose
Molecular dynamics
Numerical methods
Probability density function
Reaction kinetics
Galactofuranosyl donors
N-Dimethylmaleoyl groups
Amines
furan derivative
glucosamine
hydroxyl group
oxazolidinone derivative
trichloroacetimidic acid
article
calculation
conjugation
donor
glycosylation
priority journal
protection
reaction analysis
synthesis
Galactose
Glucosamine
Glycosylation
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v341_n9_p1096_Bohn
http://hdl.handle.net/20.500.12110/paper_00086215_v341_n9_p1096_Bohn
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario:Competitive glycosylation experiments with a galactofuranosyl trichloroacetimidate donor were performed with glucosamine acceptors having a free 4-OH group and carrying different protecting groups at N-2, O-3, and O-6. The most reactive acceptor is the N-dimethylmaleimido 3,6-di-O-benzylated derivative (6c), which reacts even faster than the oxazolidinone 1a. Molecular orbital calculations have helped to rationalize these experimental facts in terms of a hard-hard reaction occurring between the donor and the acceptor. © 2006 Elsevier Ltd. All rights reserved.

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