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Chapter 18: Synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α,β-d- glucopyranose Using the Diazo-Transfer Reagent Imidazole-1- sulfonyl Azide Hydrogen Sulfate By Garrett T. Potter, Gordon C. Jayson, John M. Gardiner, Lorenzo Guazelli, and Gavin J. Miller

Potter, Garrett T.; Jayson, Gordon C.; Gardiner, John M.; Guazelli, Lorenzo; Miller, Gavin

Authors

Garrett T. Potter

Gordon C. Jayson

John M. Gardiner

Lorenzo Guazelli



Abstract

D-Glucosamine, and derivatives thereof, are found in many biologically important saccharides, including glycosaminoglycans (GAGs), and in various classes of oligosaccharides. Glucosamines can also serve as useful chirons. Consequently, synthetic derivatizations that may have diverse applications are of value, and the con-version of the 2-amino group into a 2-azido group is a widely useful transformation. The 2-azido group both acts as a latent amine, latterly re-accessible by several reductive chemistries, and plays an important role in α-selective glycosylations. For some years, the method of choice for the amine to azide conversion was the use of freshly prepared triflic azide, but more recently the use of imidazole sulfonyl azide salts has been demonstrated as an effective and scalable alternative. This article takes into account the original safety concerns regarding the synthesis and handling/storage of these azide transfer reagents, and provides a reliable and scalable procedure for preparation of 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α,β-d-glucopyranose. It has been already employed as a highly valuable intermediate towards synthesis of heparin-like GAGs, and is also a core intermediate relevant to the wider synthesis of other GlcN-containing targets.

Citation

Potter, G. T., Jayson, G. C., Gardiner, J. M., Guazelli, L., & Miller, G. (2018). Chapter 18: Synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α,β-d- glucopyranose Using the Diazo-Transfer Reagent Imidazole-1- sulfonyl Azide Hydrogen Sulfate By Garrett T. Potter, Gordon C. Jayson, John M. Gardiner, Lorenzo Guazelli, and Gavin J. Miller. Journal of Carbohydrate Chemistry, 37(3), 178-178. https://doi.org/10.1080/07328303.2018.1455390

Journal Article Type Article
Online Publication Date Apr 25, 2018
Publication Date Mar 24, 2018
Deposit Date Jun 15, 2023
Journal Journal of Carbohydrate Chemistry
Print ISSN 0732-8303
Electronic ISSN 1532-2327
Publisher Taylor and Francis
Peer Reviewed Peer Reviewed
Volume 37
Issue 3
Pages 178-178
DOI https://doi.org/10.1080/07328303.2018.1455390
Keywords Organic Chemistry; Biochemistry
Additional Information Peer Review Statement: The publishing and review policy for this title is described in its Aims & Scope.; Aim & Scope: http://www.tandfonline.com/action/journalInformation?show=aimsScope&journalCode=lcar20; Published: 2018-04-25