A New Stereospecific Method for 1,2-cis-glycosylation

Overview

Journal Carbohydr Res

Publisher Elsevier

Specialties Biochemistry
Endocrinology

Date 1991 Jun 10

PMID 1959124

Citations 8

Authors

N K Kochetkov

E M Klimov

N N Malysheva

A V Demchenko

Affiliations

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Abstract

A new stereospecific method for 1,2-cis-glycosylation involves the reaction of 1,2-trans-glycosyl thiocyanates with sugar trityl ethers in the presence of triphenylmethylium perchlorate. The method has been applied to give disaccharide derivatives with (1----6), (1----3), and (1----2) linkages.

Citing Articles

Broadening the Scope of the Reverse Orthogonal Strategy for Oligosaccharide Synthesis.

Geringer S, Kashiwagi G, Demchenko A J Org Chem. 2022; 87(15):9887-9895.

PMID: 35862424 PMC: 9402073. DOI: 10.1021/acs.joc.2c00905.

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Singh Y, Geringer S, Demchenko A Chem Rev. 2022; 122(13):11701-11758.

PMID: 35675037 PMC: 9417321. DOI: 10.1021/acs.chemrev.2c00029.

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Panza M, Pistorio S, Stine K, Demchenko A Chem Rev. 2018; 118(17):8105-8150.

PMID: 29953217 PMC: 6522228. DOI: 10.1021/acs.chemrev.8b00051.

Stereocontrolled 1,2- glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

Nigudkar S, Demchenko A Chem Sci. 2015; 6(5):2687-2704.

PMID: 26078847 PMC: 4465199. DOI: 10.1039/C5SC00280J.

On orthogonal and selective activation of glycosyl thioimidates and thioglycosides: application to oligosaccharide assembly.

Kaeothip S, Demchenko A J Org Chem. 2011; 76(18):7388-98.

PMID: 21797272 PMC: 3170487. DOI: 10.1021/jo201117s.