Organic Letters 2008-08-21

Protecting group free glycosidations using p-toluenesulfonohydrazide donors.

Anna V Gudmundsdottir, Mark Nitz

Index: Org. Lett. 10(16) , 3461-3, (2008)

Full Text: HTML

Abstract

N'-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acetylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired beta- d-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired alcohol or transformed to the oxazoline or glycosyl azide.

Related Compounds

  • 4-Methylbenzenesul...

Related Articles:

Synthesis of some p-toluenesulfonyl-hydrazinothiazoles and hydrazino-bis-thiazoles and their anticancer activity.

2010-11-01

[Eur. J. Med. Chem. 45(11) , 5080-5, (2010)]

Vasoconstrictor-induced changes in renal blood flow: role of prostaglandins and histamine.

1988-04-01

[Am. J. Physiol. 254(4 Pt 2) , F470-6, (1988)]

Mutagenic activity of p-toluenesulfonhydrazide.

1992-01-01

[Toxicol. Ind. Health 8(6) , 369-76, (1992)]

Enantioselective synthesis of trifluoromethyl-substituted cyclopropanes.

2007-07-05

[Org. Lett. 9 , 2625, (2007)]

Dipyrazolo[1,5-a:4',3'-c]pyridines - a new heterocyclic system accessed via multicomponent reaction.

2012-01-01

[Beilstein J. Org. Chem. 8 , 2223-9, (2012)]

More Articles...