Stereoselective Synthesis of S-Linked Hexasaccharide of Landomycin A via Umpolung S-Glycosylation

Organic Letters
Kedar N Baryal, Jianglong Zhu

Abstract

Stereoselective synthesis of carbohydrate mimics resistant toward acid-mediated or enzymatic hydrolysis is chemically challenging and biologically interesting. In this Letter, the first stereoselective synthesis of a "non-hydrolyzable" S-linked hexasaccharide of antitumor antibiotic landomycin A is described. This synthesis was accomplished through the utilization of our recently developed umpolung reactivity-based S-glycosylation-sulfenylation of stereochemically defined glycosyl lithium species with asymmetric sugar-derived disulfides.

References

Jul 9, 1999·Bioorganic & Medicinal Chemistry Letters·R T CrowG A Sulikowski
Feb 6, 2002·Chembiochem : a European Journal of Chemical Biology·H Driguez
Apr 9, 2004·Journal of the American Chemical Society·Benjamin D SherryF Dean Toste
May 9, 2008·Organic Letters·Maoquan Zhou, George A O'Doherty
Dec 30, 2010·Journal of Natural Products·Khaled A ShaabanJürgen Rohr
Jul 26, 2011·Journal of the American Chemical Society·Xiaoyu YangBiao Yu
Jun 20, 2013·Angewandte Chemie·Kedar N BaryalJianglong Zhu
Aug 3, 2013·Organic Letters·John Paul IssaClay S Bennett

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Citations

May 20, 2016·Carbohydrate Research·Xiaohua LiJianglong Zhu
Oct 20, 2018·Organic & Biomolecular Chemistry·Sarbjeet KaurTing Wang

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