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...

Full description

Saved in:
Bibliographic Details
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja012383m