Issue 11, 2003
From the journal:

Chemical Communications

Preparation, X-ray structure and reactivity of a stable glycosyl iodide

Jamie Bickley,a   Jennifer A. Cottrell,a   John R. Ferguson,c   Robert A. Field,b   John R. Harding,d   David L. Hughes,b   K. P. Ravindanathan Kartha,b   Jayne L. Law,c   Feodor Scheinmannc  and  Andrew V. Stachulski*a  

* Corresponding authors

a The Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Liverpool, UK
E-mail: stachuls@liv.ac.uk
Fax: 44 (0)151 794 3588
Tel: 44 (0)151 794 3542

b Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UK

c Ultrafine UFC Ltd., Synergy House, Guildhall Close, Manchester Science Park, Manchester, UK

d AstraZeneca UK Ltd., Drug Metabolism and Pharmacokinetics Department, Mereside, Alderley Park, Macclesfield, Cheshire, UK

Abstract

Highly selective reaction of methyl tetra-O-pivaloyl-β-D-glucopyranuronate 2 with iodotrimethylsilane or (Me3Si)2 and I2 affords, in excellent yield, the ‘disarmed’ glycosyl iodide 1 which has good stability at 20 °C and excellent stability at 0 °C; the X-ray crystal structure of 1 is described, along with a comparison of its utility as a glycosyl donor to that of the corresponding bromide.

Graphical abstract: Preparation, X-ray structure and reactivity of a stable glycosyl iodide

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Article information

DOI
https://doi.org/10.1039/B302629A
Article type
Communication
Submitted
07 Mar 2003
Accepted
02 Apr 2003
First published
01 May 2003

Chem. Commun., 2003, 1266-1267

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Preparation, X-ray structure and reactivity of a stable glycosyl iodide

J. Bickley, J. A. Cottrell, J. R. Ferguson, R. A. Field, J. R. Harding, D. L. Hughes, K. P. Ravindanathan Kartha, J. L. Law, F. Scheinmann and A. V. Stachulski, Chem. Commun., 2003, 1266 DOI: 10.1039/B302629A

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