scispace - formally typeset
Journal ArticleDOI

The reactions of nitrosyl chloride and dinitrogen tetroxide with acetylated glycals. Acetylated 2-deoxy-2-nitroso-α-D-hexopyranosyl chlorides and nitrates and acetylated 2-nitroglycals

R. U. Lemieux, +2 more
- 01 Feb 1968 - 
- Vol. 46, Iss: 3, pp 413-418
TLDR
In this paper, the mechanisms of these reactions are discussed and a high degree of stereospecificity is obtained for dimeric 1,2-cis-2,deoxy-2-nitroso-α-D-aldopyranosyl chlorides.
Abstract
Reaction of nitrosyl chloride with acetylated glycals affords, with a high degree of stereospecificity, dimeric acetylated 1,2-cis-2-deoxy-2-nitroso-α-D-aldopyranosyl chlorides. Reaction of acetylated glycals with dinitrogen tetroxide, depending on the reaction conditions, can give either acetylated 2-deoxy-2-nitroso-α-D-aldopyranosyl nitrates as dimers or acetylated 2-nitroglycals. The mechanisms of these reactions are discussed.

read more

Citations
More filters
Journal ArticleDOI

New principles for glycoside-bond formation.

TL;DR: New principles for the formation of glycoside bonds are discussed and developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.
Journal ArticleDOI

Results and Problems of O-Glycoside Synthesis

Günter Wulff, +1 more
- 01 Mar 1974 - 
TL;DR: The present progress report surveys recent developments in the formation of O-glycosidic bonds starting from 1-halo sugars and from sugar 1,2-orthoesters.
Journal ArticleDOI

Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars.

TL;DR: The discovery of new methods for stereoselective glycoside synthesis and convergent oligosaccharide assembly has been critical for the area of glycosciences and the current standing in the field is evaluated.
Journal ArticleDOI

Catalytic Glycosylations in Oligosaccharide Synthesis

TL;DR: All methods of catalytic glycosylation with the focus on the development and application in oligosaccharide synthesis and an overview of the scope and limitations of these are provided.
Journal ArticleDOI

Preparations of C-Nitroso Compounds

TL;DR: In this review, a comprehensive review of the synthetic procedures for the preparation of C-nitroso compounds are presented and place these procedures in proper historical context.
Related Papers (5)