Tuneable regioselectivity during the mono-etherification of the 2,3-diol of a mannose derivative This paper is dedicated to the memory of the late Dr. John M. Webber, distinguished carbohydrate chemist and founding editor of Carbohydrate Research

Sigþór Pétursson*, Sean Michael Scully, Sigríður Jónsdóttir

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)37-43
Number of pages7
JournalCarbohydrate Research
Volume388
Issue number1
DOIs
Publication statusPublished - 31 Mar 2014

Bibliographical note

Funding Information:
The University of Akureyri Science Fund is thanked for financial support and the Science Institute, University of Iceland, is thanked for the provision of spectroscopic facilities.

Other keywords

  • Catalysis
  • Diol
  • Protection
  • Regioselectivity
  • Tin(II) chloride

Fingerprint

Dive into the research topics of 'Tuneable regioselectivity during the mono-etherification of the 2,3-diol of a mannose derivative This paper is dedicated to the memory of the late Dr. John M. Webber, distinguished carbohydrate chemist and founding editor of Carbohydrate Research'. Together they form a unique fingerprint.

Cite this