An Efficient Method for Catalytic and Stereoselective Synthesis of 2-Deoxy-α-D-glucopyranosides from 3,4,6,-Tri-O-benzyl-2-deoxy-D-glucopyranose and Several Alcoholic Nucleophiles

doi:10.1246/CL.1997.969

Paper

An Efficient Method for Catalytic and Stereoselective Synthesis of 2-Deoxy-α-D-glucopyranosides from 3,4,6,-Tri-O-benzyl-2-deoxy-D-glucopyranose and Several Alcoholic Nucleophiles

Published Oct 1, 1997 · Kazuya Takeuchi, Satoshi Higuchi, T. Mukaiyama

Chemistry Letters

Q2 SJR score

22

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0

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Abstract

Several 2-deoxy-α-D-glucopyranosides are stereoselectively synthesized in high yields by glycosylation of various alcoholic nucleophiles with 3,4,6-tri-O-benzyl-2-deoxy-glucopyranose using a catalytic amount of trityl tetrakis(pentafluorophenyl)borate.

Study Snapshot

This method efficiently synthesizes various 2-deoxy--D-glucopyranosides in high yields by glycosylating various alcoholic nucleophiles with 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose and trityl

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

An Efficient Method for Catalytic and Stereoselective Synthesis of 2-Deoxy-α-D-glucopyranosides from 3,4,6,-Tri-O-benzyl-2-deoxy-D-glucopyranose and Several Alcoholic Nucleophiles

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References

2-bromo-2-deoxy sugars as starting materials for the synthesis of α- or β-glycosides of 2-deoxy sugars

2-bromo-2-deoxy sugars can be used to synthesize - or -glycosides of 2-deoxy sugars, with high yields achieved for -d-glycosides.

A novel synthesis of 2-deoxy-α-glycosides

This study presents a novel synthesis of 2-deoxy--glycosides using glycals, alcohols, and N-bromosuccinimide, with high yields and stereoselectivity.

A stereospecific approach towards the synthesis of 2-deoxy α- and β-glycosides based on a 1,2-ethyl (phenyl) thio group migration

This study presents a stereospecific approach for the synthesis of 2-deoxy - and -glycosides using 1,2-ethyl (phenyl) thio group migration.

Stereoselective synthesis of α-linked 2-deoxysaccharides and furanosaccharides by use of 2-deoxy 2-pyridyl-1-thio pyrano- and furanosides as donors and methyl iodide as an activator

This study presents a highly stereoselective glycosidation methodology for synthesis of axially linked 2-deoxysaccharides and -linked furanosaccharides using 2-deoxy 2-pyridyl-1-thiopyranoside donors and methyl iodide

Citations

Trityl tetrakis(pentafluorophenyl)borate: A sustainable precursor for multifunctional silylium Lewis acid organocatalysis

Trityl tetrakis(pentafluorophenyl)borate is a sustainable, metal-free catalyst for multifunctional silylium Lewis acid organocatalysis, enabling diverse transformations like hydrosilylation, reduction, activation, and bond formation.

4,5-Dioxo-imidazolinium Cation-Promoted α-Selective Dehydrative Glycosylation of 2-Deoxy- and 2,6-Dideoxy Sugars.

The 4,5-dioxo-imidazolinium cation activation strategy with geminal dichloroimidazolidinediones (DCIDs) effectively promotes dehydrative glycosylation reactions between 2-deoxy- and 2,6-dideoxy-sugar hem

Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester.

An N-methylpyridinium-4-boronic ester catalyzes dehydrative glycosidations of 2-deoxy sugar-derived hemiacetals, enabling C-O bond formation from carbohydrate-derived hemiacetals.

Direct Dehydrative Glycosylation of C1-Alcohols.

Direct dehydrative glycosylation of C1-alcohols offers advantages in preparation, stability, and reactivity, making it a promising method for studying carbohydrates' essential functions and applications in total synthesis.

Catalytic Glycosylations in Oligosaccharide Synthesis.

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