Journal ArticleDOI
Can the stereochemical outcome of glycosylation reactions be controlled by the conformational preferences of the glycosyl donor
TLDR
A strategy to design face discriminated glycosyl donors that exist predominantly in only one family of conformers is proposed based on observations of high beta-stereoselectivity of mannopyranosyl donors and high alpha-stirring of glucopyranoyl donors with the 4,6-O-benzylidene protecting groups.About:
This article is published in Carbohydrate Research.The article was published on 2002-04-17. It has received 96 citations till now. The article focuses on the topics: Ring flip & Glycosyl donor.read more
Citations
More filters
Journal ArticleDOI
New principles for glycoside-bond formation.
Xiangming Zhu,Richard R. Schmidt +1 more
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
Mechanism of chemical O-glycosylation: from early studies to recent discoveries.
TL;DR: The main focus of this perspective lies in the discussion of the recent mechanistic theories and supporting experimental evidences that have been put forth in an attempt to advance the understanding of the factors affecting chemical glycosylation.
Journal ArticleDOI
Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.
TL;DR: The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.
Journal ArticleDOI
The disarming effect of the 4,6-acetal group on glycoside reactivity: torsional or electronic?
TL;DR: It is shown that the hydroxymethyl rotamers deactivate the rate of glycoside hydrolysis in the order tg >> gt > gg, and that the deactivating effect of the 4,6-methylene group is partially torsional and partially electronic.
Journal ArticleDOI
The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1–SN2 Interface
TL;DR: A critical review of the state-of-the-art evidence in support of the mechanisms of glycosylation reactions is provided, and the use of kinetic isotope effects for the determination of transition-state structure is presented.
References
More filters
Journal ArticleDOI
General definition of ring puckering coordinates
Dieter Cremer,John A. Pople +1 more
TL;DR: In this article, a unique mean plane is defined for a general monocyclic puckered ring, which is described by amplitude and phase coordinates which are generalizations of those introduced for cyclopentane by Kilpatrick, Pitzer, and Spitzer.
Book
Studies in natural products chemistry
TL;DR: The series covers the synthesis or testing and recording of the medicinal properties of natural products, providing cutting edge accounts of the fascinating developments in the isolation, structure elucidation, synthesis, biosynthesis and pharmacology of a diverse array of bioactive natural products.
Journal ArticleDOI
Recent progress in O-glycosylation methods and its application to natural products synthesis
Kazunobu Toshima,Kuniaki Tatsuta +1 more
Journal ArticleDOI
Automated Solid-Phase Synthesis of Oligosaccharides
TL;DR: Access to certain complex oligosaccharides now has become feasible in a fashion much like the construction of oligopeptides and oligonucleotides.
Related Papers (5)
Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and 1H, 13C, and 19F NMR Spectroscopic Investigation
David Crich and,Sanxing Sun +1 more