The Trityl Tetrakis(pentafluorophenyl)borate Catalyzed Stereoselective Glycosylation Using New Glycosyldonor, 3,4,6-Tri-O-benzyl-2-O-p-toluoyl-β-D-glucopyranosyl Phenylcarbonate

doi:10.1246/CL.2000.122

Paper

The Trityl Tetrakis(pentafluorophenyl)borate Catalyzed Stereoselective Glycosylation Using New Glycosyldonor, 3,4,6-Tri-O-benzyl-2-O-p-toluoyl-β-D-glucopyranosyl Phenylcarbonate

Published Feb 1, 2000 · Kazuya Takeuchi, Takayuki Tamura, T. Mukaiyama

Chemistry Letters

Q2 SJR score

14

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

The trityl tetrakis(pentafluorophenyl)borate [TrB(C6F5)4] catalyzed stereoselective synthesis of various disaccharides was successfully carried out by treating a new 2-O-acyl-protected glycosyl donor, 3,4,6-tri-O-benzyl-2-O-p-toluoyl-β-D-glucopyranosyl phenylcarbonate, with several glycosyl acceptors, thioglycosides, affording the corresponding disaccharides in high yields.

Study Snapshot

The trityl tetrakis(pentafluorophenyl)borate catalyzed stereoselective synthesis of various disaccharides using a new glycosyl donor, 3,4,6-tri-O-benzyl-2-O-p-

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

The Trityl Tetrakis(pentafluorophenyl)borate Catalyzed Stereoselective Glycosylation Using New Glycosyldonor, 3,4,6-Tri-O-benzyl-2-O-p-toluoyl-β-D-glucopyranosyl Phenylcarbonate

Sign up to use Study Snapshot

References

Solid-Phase Synthesis of Oligosaccharides: Construction of a Dodecasaccharide.

This solid-phase strategy allows for the construction of complex oligosaccharides like dodecasaccharide 1 by attaching them to a polymeric support and using thioglycosides as carbohydrate donors.

Glycosyl transfer by isopropenyl glycosides: Trisaccharide synthesis in one pot by selective coupling of isopropenyl and n-pentenyl glycopyranosides

Selective coupling of isopropenyl and n-pentenyl glycopyranosides allows for efficient trisaccharide synthesis in a single pot, yielding 25% trisaccharide in 25% yield.

One-pot sequential glycosylation: A new method for the synthesis of oligosaccharides

One-pot sequential glycosylation is a new method for synthesizing oligosaccharides and trisaccharides using various glycosidic donors.

One-Pot Synthesis of Substituted Allyl-α-d-Glucopyranosides by an in situ Anomerization Protocol

This new 3-step, 1-pot procedure allows for the stereoselective -glycosylation of substituted allylic alcohols, with the key step being in situ anomerization of the -glycoside upon treatment with TiCl4.

Citations

Catalytic Glycosylations in Oligosaccharide Synthesis.

Catalytic glycosylation methods have revolutionized oligosaccharide synthesis, with potential for future advancements and applications in various fields.

In Situ Preactivation Strategies for the Expeditious Synthesis of Oligosaccharides: A Review

Advances in synthetic carbohydrate chemistry, such as preactivation methodologies, enable rapid synthesis of useful oligosaccharides, with potential applications in biomedicine and pharmaceuticals.

Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.

Selective activation of one leaving group over another, combined with orthogonal strategies, allows for rapid oligosaccharide synthesis by minimizing extraneous chemical manipulations.

Glycan Synthesis: Key Strategies

Chemical synthesis is the most common approach for synthesising glycans, offering advantages and disadvantages, while enzymatic synthesis offers potential for structurally defined material.

Hg(OTf)2-catalyzed glycosylation using alkynoate as the leaving group

The novel Hg(OTf)2-catalyzed glycosylation procedure using alkynoic acid residues offers efficient and mild glycosylation of hindered alcohols under mild reaction conditions.