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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2006
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| 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 |
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paper:paper_00086215_v341_n9_p1096_Bohn2023-06-08T14:32:53Z A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor Stortz, Carlos Arturo Competitive glycosylations DFT Galactofuranosyl donor Glucosamine acceptors N-Dimethylmaleoyl group Conformations Glucose Molecular dynamics Numerical methods Probability density function Reaction kinetics Competitive glycosylations Galactofuranosyl donors Glucosamine acceptors 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 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. Fil:Stortz, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2006 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 |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Competitive glycosylations DFT Galactofuranosyl donor Glucosamine acceptors N-Dimethylmaleoyl group Conformations Glucose Molecular dynamics Numerical methods Probability density function Reaction kinetics Competitive glycosylations Galactofuranosyl donors Glucosamine acceptors 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 |
| spellingShingle |
Competitive glycosylations DFT Galactofuranosyl donor Glucosamine acceptors N-Dimethylmaleoyl group Conformations Glucose Molecular dynamics Numerical methods Probability density function Reaction kinetics Competitive glycosylations Galactofuranosyl donors Glucosamine acceptors 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 Stortz, Carlos Arturo A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor |
| topic_facet |
Competitive glycosylations DFT Galactofuranosyl donor Glucosamine acceptors N-Dimethylmaleoyl group Conformations Glucose Molecular dynamics Numerical methods Probability density function Reaction kinetics Competitive glycosylations Galactofuranosyl donors Glucosamine acceptors 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 |
| description |
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. |
| author |
Stortz, Carlos Arturo |
| author_facet |
Stortz, Carlos Arturo |
| author_sort |
Stortz, Carlos Arturo |
| title |
A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor |
| title_short |
A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor |
| title_full |
A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor |
| title_fullStr |
A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor |
| title_full_unstemmed |
A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor |
| title_sort |
comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor |
| publishDate |
2006 |
| url |
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 |
| work_keys_str_mv |
AT stortzcarlosarturo acomparativestudyoftheinfluenceofsomeprotectinggroupsonthereactivityofdglucosamineacceptorswithagalactofuranosyldonor AT stortzcarlosarturo comparativestudyoftheinfluenceofsomeprotectinggroupsonthereactivityofdglucosamineacceptorswithagalactofuranosyldonor |
| _version_ |
1768546236025012224 |