First synthesis of a digitalis saponin. Demonstration of the scope and limitations of a convergent scheme for branched oligosaccharide synthesis by the logic of glycal assembly Journal Article


Authors: Randolph, J. T.; Danishefsky, S. J.
Article Title: First synthesis of a digitalis saponin. Demonstration of the scope and limitations of a convergent scheme for branched oligosaccharide synthesis by the logic of glycal assembly
Abstract: The synthesis of complex glycosides, with branching at C2, is demonstrated. The key element involves the use of a 1, 2-oxirane donor. Upon glycosylation, a C2 hydroxyl is exposed to serve as the acceptor in the next glycosylation. Branching at C2 with a β-linked glycoside at C1 was not achievable with epoxy 23 donor, but was accomplished with fluoro donor 25, in turn derived from 23. (See 19 + 18 → 20; 20 + 25 → 26. Compound 26 was deprotected to complete the first total synthesis of a natural saponin, desgalactotigonin (3)). A limitation in stereospecifity in the use of donor 23 and monoprotected galactal acceptor 28 was also encountered. © 1995, American Chemical Society. All rights reserved.
Keywords: unclassified drug; methodology; drug synthesis; nuclear magnetic resonance; reaction analysis; stereochemistry; glycoside; saponin; article; degalactotigonin
Journal Title: Journal of the American Chemical Society
Volume: 117
Issue: 21
ISSN: 0002-7863
Publisher: American Chemical Society  
Date Published: 1995-05-31
Start Page: 5693
End Page: 5700
Language: English
DOI: 10.1021/ja00126a010
PROVIDER: scopus
DOI/URL:
Notes: Article -- Export Date: 28 August 2018 -- Source: Scopus
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