Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor

An assessment of the relative O-3/O-4 reactivities of both α- and β-methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a d-glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylat...

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Detalles Bibliográficos
Autor principal: Stortz, Carlos Arturo
Publicado: 2013
Materias:
Glucosamine
Glycosylation
Benzyl group
Glycosyl donors
Methyl glycosides
Esterification
carbonyl derivative
disaccharide
glucopyranoside
glucosamine derivative
glycoside
hexosamine
hydroxyl group
acetylation
article
carbohydrate analysis
conformation
glycosylation
hydrogen bond
nucleophilicity
priority journal
stereochemistry
Carbohydrate Conformation
Hexosamines
Oxygen
Stereoisomerism
Substrate Specificity
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v380_n_p167_DellaFelice
http://hdl.handle.net/20.500.12110/paper_00086215_v380_n_p167_DellaFelice
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_00086215_v380_n_p167_DellaFelice
record_format dspace
spelling paper:paper_00086215_v380_n_p167_DellaFelice2023-06-08T14:33:04Z Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor Stortz, Carlos Arturo Glucosamine Glycosylation Benzyl group Glycosyl donors Methyl glycosides Esterification carbonyl derivative disaccharide glucopyranoside glucosamine derivative glycoside hexosamine hydroxyl group acetylation article carbohydrate analysis conformation glycosylation hydrogen bond nucleophilicity priority journal stereochemistry Carbohydrate Conformation Glycosylation Hexosamines Oxygen Stereoisomerism Substrate Specificity An assessment of the relative O-3/O-4 reactivities of both α- and β-methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a d-glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. © 2013 Elsevier Ltd. All rights reserved. Fil:Stortz, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2013 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v380_n_p167_DellaFelice http://hdl.handle.net/20.500.12110/paper_00086215_v380_n_p167_DellaFelice
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Glucosamine
Glycosylation
Benzyl group
Glycosyl donors
Methyl glycosides
Esterification
carbonyl derivative
disaccharide
glucopyranoside
glucosamine derivative
glycoside
hexosamine
hydroxyl group
acetylation
article
carbohydrate analysis
conformation
glycosylation
hydrogen bond
nucleophilicity
priority journal
stereochemistry
Carbohydrate Conformation
Glycosylation
Hexosamines
Oxygen
Stereoisomerism
Substrate Specificity
spellingShingle Glucosamine
Glycosylation
Benzyl group
Glycosyl donors
Methyl glycosides
Esterification
carbonyl derivative
disaccharide
glucopyranoside
glucosamine derivative
glycoside
hexosamine
hydroxyl group
acetylation
article
carbohydrate analysis
conformation
glycosylation
hydrogen bond
nucleophilicity
priority journal
stereochemistry
Carbohydrate Conformation
Glycosylation
Hexosamines
Oxygen
Stereoisomerism
Substrate Specificity
Stortz, Carlos Arturo
Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor
topic_facet Glucosamine
Glycosylation
Benzyl group
Glycosyl donors
Methyl glycosides
Esterification
carbonyl derivative
disaccharide
glucopyranoside
glucosamine derivative
glycoside
hexosamine
hydroxyl group
acetylation
article
carbohydrate analysis
conformation
glycosylation
hydrogen bond
nucleophilicity
priority journal
stereochemistry
Carbohydrate Conformation
Glycosylation
Hexosamines
Oxygen
Stereoisomerism
Substrate Specificity
description An assessment of the relative O-3/O-4 reactivities of both α- and β-methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a d-glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. © 2013 Elsevier Ltd. All rights reserved.
author Stortz, Carlos Arturo
author_facet Stortz, Carlos Arturo
author_sort Stortz, Carlos Arturo
title Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor
title_short Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor
title_full Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor
title_fullStr Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor
title_full_unstemmed Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: Effect of a conformationally armed (superarmed) glycosyl donor
title_sort differential o-3/o-4 selectivity in the glycosylation of n-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
publishDate 2013
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v380_n_p167_DellaFelice
http://hdl.handle.net/20.500.12110/paper_00086215_v380_n_p167_DellaFelice
work_keys_str_mv AT stortzcarlosarturo differentialo3o4selectivityintheglycosylationofndimethylmaleoylprotectedhexosamineacceptorseffectofaconformationallyarmedsuperarmedglycosyldonor
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