Journal
ORGANIC LETTERS
Volume 17, Issue 18, Pages 4530-4533Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02223
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Funding
- National Science Foundation [CHE-1213352]
- Ohio Cancer Research Associates
- University of Toledo
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1213352] Funding Source: National Science Foundation
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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.
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