Unexpected Role of O-2 “Protecting” Groups of Glycosyl Donors in Mediating Regioselective Glycosidation

Glycosidation of several vicinal diols reveals that exquisite regioselectivity can be achieved by using 2-O-benzoyl n-pentenyl glycoside donors and/or their cyclic 1,2-ortho ester counterparts. The regioselective preferences for both are the same, although ratios and yields may differ. In stark cont...

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Published in:Journal of the American Chemical Society 2002-04, Vol.124 (13), p.3198-3199
Main Authors: Fraser-Reid, Bert, Lopez, J. Cristobal, Radhakrishnan, K. V, Mach, Mateusz, Schlueter, Urs, Gomez, Ana M, Uriel, Clara
Format: Article
Language:English
Subjects:
Carbohydrate Conformation
Chemical reactivity
Chemistry
Exact sciences and technology
Glycosides - chemical synthesis
Glycosides - chemistry
Organic chemistry
Reactivity and mechanisms
Structure-Activity Relationship
Substrate Specificity
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container_issue 13
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container_title Journal of the American Chemical Society
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creator Fraser-Reid, Bert
Lopez, J. Cristobal
Radhakrishnan, K. V
Mach, Mateusz
Schlueter, Urs
Gomez, Ana M
Uriel, Clara
description Glycosidation of several vicinal diols reveals that exquisite regioselectivity can be achieved by using 2-O-benzoyl n-pentenyl glycoside donors and/or their cyclic 1,2-ortho ester counterparts. The regioselective preferences for both are the same, although ratios and yields may differ. In stark contrast, glycosidation of the diols with the corresponding 2-O-benzylated donors gives poor, if any, regioselectivity.
doi_str_mv 10.1021/ja012383m
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Carbohydrate Conformation
Chemical reactivity
Chemistry
Exact sciences and technology
Glycosides - chemical synthesis
Glycosides - chemistry
Organic chemistry
Reactivity and mechanisms
Structure-Activity Relationship
Substrate Specificity
title Unexpected Role of O-2 “Protecting” Groups of Glycosyl Donors in Mediating Regioselective Glycosidation
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