Literature DB >> 24607539

Tuneable regioselectivity during the mono-etherification of the 2,3-diol of a mannose derivative.

Sigthor Petursson1, Sean M Scully2, Sigridur Jonsdottir3.   

Abstract

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.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Catalysis; Diol; Protection; Regioselectivity; Tin(II) chloride

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Substances:

Year:  2014        PMID: 24607539     DOI: 10.1016/j.carres.2014.02.016

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  1 in total

1.  Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions.

Authors:  Kyle T Howard; Brian C Duffy; Matthew R Linaburg; John D Chisholm
Journal:  Org Biomol Chem       Date:  2016-02-07       Impact factor: 3.876

  1 in total

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