| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1387891 | Carbohydrate Research | 2014 | 7 Pages |
Abstract
•Regioselectivity for either the 3- or the 2-hydroxyl group of a manno-pyranoside.•Catalyst concentration dependence of selectivity.•Different diaryldiazomethanes give different regioselectivity.
The paper reports selective mono-etherification of the 2-, and 3-hydroxyl groups of methyl 4,6-O-isopropylidene-α-d-mannopyranoside using tin(II) chloride catalysed reactions of diaryldiazomethanes. By the use of different diazo compounds and the variation of the tin(II) chloride concentration the ether formation can be shifted from over 90% 3-selectivity to over 90% 2-selectivity.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Sigthor Petursson, Sean M. Scully, Sigridur Jonsdottir,