PDF icon PDF herunterladen
Synthesis 2000; 2000(2): 259-264
DOI: 10.1055/s-2000-6251
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

 als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

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