Carbohydrate research

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

G Pistia-Brueggeman, RI Hollingsworth

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

Full Text: HTML

Citation Number: 10

Abstract

The o-nitrophenyl group, a protecting group with latent activation potential, was used as a protecting group for the glycosidic position. It is stable to common conditions used in synthesis and can be activated for displacement and glycoside formation by an alcohol, using zinc chloride as a catalyst. Good to excellent yields of β-glycosides of the important amino sugar N-acetylglucosamine were obtained. A mechanism for the reaction is ...

Related Articles:

Protecting group free glycosidations using p-toluenesulfonohydrazide donors

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

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

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

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...