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Synthesis 2000; 2000(2): 259-264
DOI: 10.1055/s-2000-6251
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Synthesis of Nojirimycinyl C-(l)-Serine

Thomas Fuchs* , Richard R. Schmidt
  • *Fakultät Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany; Fax +49 (75 31) 88 31 35
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Publication Date:
31 December 2000 (online)

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Ozonolysis of C-allyl nojirimycin 5 furnished aldehyde 6; ensuing Wittig-Horner reaction with glycine derived phosphonate 9 afforded α-acylaminoacrylate 10. Concomitant hydrogenation of the C=C double bond and hydrogenolytic cleavage of the benzyloxycarbonyl protective group gave mainly the desired nojirimycinyl C-(l)-serine derivative (l)-11, which was transformed into suitable building blocks for the synthesis of novel glycopeptides. The configuration of (l)-11 was assigned with the help of the Dale-Mosher method.

C-glycosides - glycopeptide analogs - glycosidase inhibitors - nojirimycin

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