Total synthesis of glycononaosyl ceramide with a sialyl dimeric Lex sequence View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1996-04

AUTHORS

Masami Iida, Akira Endo, Shuji Fujita, Masaaki Numata, Kazuo Suzuki, Shigeki Nunomura, Tomoya Ogawa

ABSTRACT

The first total synthesis of glycononaosyl ceramide with a sialyl dimeric Le(x) sequence 1 is described. Regio- and stereo-selective glycosylations of sialyl donors 6,7,8 with the suitably protected Le(x) trisaccharide acceptors 9,10 beta were performed to give the expected tetrasaccharides 15 and 21, which were converted into the corresponding donors 20 and 22. Boron trifluoride etherate-promoted glycosylation of 20 with pentasaccharide acceptor 11 afforded regioselectively the expected nonasaccharide 23. After replacing benzyl groups of 23 by acetyl groups, the anomeric acetate was transformed into the alpha-trichloroacetimidate 27. The crucial coupling between 27 and (2S, 3R, 4E-3-O-benzoyl-2-N-tetracosanoylsphingenine 3 was executed to afford completely protected beta-glycoside 28. Finally, selective cleavage of the methyl ester and N,O-deprotection of 28 gave the target ganglioside 1. More... »

PAGES

203-211

References to SciGraph publications

  • 1984-09. An efficient synthesis of ceramide fromd-glucose in GLYCOCONJUGATE JOURNAL
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/bf00731495

    DOI

    http://dx.doi.org/10.1007/bf00731495

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1012261444

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/8737245


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