Regenerative Glycosylation

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2017 Dec 12

PMID 29227649

Citations 20

Authors

Yashapal Singh

Tinghua Wang

Scott A Geringer

Keith J Stine

Alexei V Demchenko

Affiliations

Soon will be listed here.

Abstract

Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.

Citing Articles

SFox imidates as versatile glycosyl donors for chemical glycosylation.

DAmico A, Shrestha G, Das A, Stine K, Demchenko A Org Biomol Chem. 2024; 22(25):5214-5223.

PMID: 38867654 PMC: 11583801. DOI: 10.1039/d4ob00679h.

Pathophysiological Aspects and Therapeutic Armamentarium of Alzheimer's Disease: Recent Trends and Future Development.

Dave B, Shah Y, Maheshwari K, Mansuri K, Prajapati B, Postwala H Cell Mol Neurobiol. 2023; 43(8):3847-3884.

PMID: 37725199 PMC: 11407742. DOI: 10.1007/s10571-023-01408-7.

N-Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile.

Shrestha G, Panza M, Singh Y, Stine K, Demchenko A European J Org Chem. 2022; 2022(18).

PMID: 36339352 PMC: 9635513. DOI: 10.1002/ejoc.202200300.

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.

HPLC-Based Automated Synthesis of Glycans in Solution.

Escopy S, Singh Y, Stine K, Demchenko A Chemistry. 2022; 28(39):e202201180.

PMID: 35513346 PMC: 9403992. DOI: 10.1002/chem.202201180.

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