Synthesis of human cancer associated globo-H (MBR1) Glycosylamino acid: Some mechanistic and conformational reinvestigations Journal Article

   


Authors: Zhu, J.; Wan, Q.; Yang, G.; Ouerfelli, O.; Danishefsky, S. J.
Article Title: Synthesis of human cancer associated globo-H (MBR1) Glycosylamino acid: Some mechanistic and conformational reinvestigations
Abstract: The synthesis of an extended globo-H (MBrl antigen) in the form of a glycosylamino acid is reported. By careful NMR analysis, we found an interesting conformational "flip" on the E ring of some synthetic intermediates. An explanation offered for the successful |3+3] coupling of ABC acceptor 11 and DEF donor 10 possessing a C4 free hydroxyl to produce β-galactoside in azaglycosidations is reinforced. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.
Keywords: total synthesis; carbohydrate; globo-h; glycosylamino acid; nmr spectral analysis
Journal Title: Heterocycles
Volume: 79
Issue: 1
ISSN: 0385-5414
Publisher: Pergamon-Elsevier Science Ltd  
Date Published: 2009-04-01
Start Page: 441
End Page: 449
Language: English
DOI: 10.3987/com-08-s(d)82
PROVIDER: scopus
PMCID: PMC3059307
PUBMED: 21423783
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-67651091795&partnerID=40&md5=f806620060936522ea188625bd13c74f
Notes: --- - "Cited By (since 1996): 3" - "Export Date: 30 November 2010" - "CODEN: HTCYA" - "Source: Scopus"
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MSK Authors
  1. Qian Wan
    23 Wan
  2. Jianglong Zhu
    14 Zhu
  3. Samuel J Danishefsky
    539 Danishefsky
  4. Ouathek Ouerfelli
    100 Ouerfelli
  5. Guangbin Yang
    27 Yang
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