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Letter

Facile Approach to 2-Acetamido-2-deoxy-β-d-Glucopyranosides via a Furanosyl Oxazoline

Supporting Info

Ye Cai, Chang-Chun Ling, and David R. Bundle*

Alberta Ingenuity Center for Carbohydrate Science, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2 Canada

Org. Lett., 2005, 7 (18), pp 4021–4024

DOI: 10.1021/ol051523k

Publication Date (Web): August 11, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, dave.bundle@ualberta.ca

Abstract

A concise and convenient route that may be easily scaled is reported for the preparation of unprotected β-glucopyranosides of N-acetyl-d-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding β-d-glucopyranosides in good to high yields. Primary alcohols gave only β-d-glucopyranosides. A mechanism is proposed for this transformation.

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Published In Issue September 01, 2005
Received June 29, 2005

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Letter

Facile Approach to 2-Acetamido-2-deoxy-β-d-Glucopyranosides via a Furanosyl Oxazoline

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Synthesis of Vinylcycloheptadienes by the Nickel-Catalyzed Three-Component [3 + 2 + 2] Cocyclization. Application to the Synthesis of Polycyclic Compounds

Oxazolidinone Protected 2-Amino-2-deoxy-d-glucose Derivatives as Versatile Intermediates in Stereoselective Oligosaccharide Synthesis and the Formation of α-Linked Glycosides

Ganglioside GQ1b: Efficient Total Synthesis and the Expansion to Synthetic Derivatives To Elucidate Its Biological Roles

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