Organic letters

Facile approach to 2-acetamido-2-deoxy-β-D-glucopyranosides via a furanosyl oxazoline

Y Cai, CC Ling, DR Bundle

Index: Cai, Ye; Ling, Chang-Chun; Bundle, David R. Organic Letters, 2005 , vol. 7, # 18 p. 4021 - 4024

Full Text: HTML

Citation Number: 51

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.

Related Articles:

The use of the o-nitrophenyl group as a protecting/activating group for 2-acetamido-2-deoxyglucose

[Pistia-Brueggeman, Gabriela; Hollingsworth, Rawle I. Carbohydrate Research, 2003 , vol. 338, # 5 p. 455 - 458]

Protecting group free glycosidations using p-toluenesulfonohydrazide donors

[Gudmundsdottir, Anna V.; Nitz, Mark Organic Letters, 2008 , vol. 10, # 16 p. 3461 - 3463]

The use of the o-nitrophenyl group as a protecting/activating group for 2-acetamido-2-deoxyglucose

[Pistia-Brueggeman, Gabriela; Hollingsworth, Rawle I. Carbohydrate Research, 2003 , vol. 338, # 5 p. 455 - 458]

The use of the o-nitrophenyl group as a protecting/activating group for 2-acetamido-2-deoxyglucose

[Pistia-Brueggeman, Gabriela; Hollingsworth, Rawle I. Carbohydrate Research, 2003 , vol. 338, # 5 p. 455 - 458]

Moenomycin a: spaltung des antibiotikums mit trifluoressigsäure/2-propanol und bestimmung der verknüpfung von d-glucose und 2-acetamido-2-desoxy-d-glucose

[Welzel; Knupp; Witteler; et al. Tetrahedron, 1981 , vol. 37, # 1 p. 97 - 104]

More Articles...