Application of the glycal assembly method to the concise synthesis of neoglycoconjugates of Le(y) and Le(b) blood group determinants and of H-type I and H-type II oligosaccharides Journal Article

  


Authors: Danishefsky, S. J.; Behar, V.; Randolph, J. T.; Lloyd, K. O.
Article Title: Application of the glycal assembly method to the concise synthesis of neoglycoconjugates of Le(y) and Le(b) blood group determinants and of H-type I and H-type II oligosaccharides
Abstract: The power of the glycal assembly strategy for reaching Lewis and H-type blood group determinants is demonstrated herein. Three key elements form the basis of the method. Thus, a-epoxides derived from galactal cyclic carbonate 13 are produced stereospecifically and are highly effective β-galactosyl donors. Also, 6-monoprotected glucals can be regiospecifically glycosylated at the C3 hydroxyl (see 23 + 13 → 24). Moreover, glycosylation via a glycal epoxide produces a unique C2 hydroxyl in the product which can be exploited as the acceptor site for branching (see formation of 26). © 1995, American Chemical Society. All rights reserved.
Keywords: methodology; epitope; oligosaccharide; blood group lewis system; carbohydrate synthesis; article
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: 5701
End Page: 5711
Language: English
DOI: 10.1021/ja00126a011
PROVIDER: scopus
DOI/URL:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0029002924&doi=10.1021%2fja00126a011&partnerID=40&md5=412e03e662af4a37ee0311f65646735d
Notes: Article -- Export Date: 28 August 2018 -- Source: Scopus
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MSK Authors
  1. Samuel J Danishefsky
    539 Danishefsky
  2. Kenneth O Lloyd
    163 Lloyd
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