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Synthesis of naphthoxylosides on solid support

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Author

Summary, in English

In order to investigate the selective antiproliferative effects shown by 2-(6-hydroxynaphthyl)-beta-D-xylopyranoside the 14 possible beta-D-xylopyranosidic compounds were synthesized on solid support. An aminomethylated polystyrene resin was converted into an acid chloride resin and then esterified using dihydroxynaphthalene. The free hydroxy group was then xylosylated Under BF3.OEt2 mediated conditions. The xyloside was deprotected and simultaneously cleaved off the resin Using NaOMe/MeOH. Final purification using reverse phase HPLC gave the pure xylosides in 6-42% yield with Virtually no formation of alpha-xylosides. (C) 2002 Elsevier Science Ltd. All rights reserved.

Publishing year

2002

Language

English

Pages

6549-6552

Publication/Series

Tetrahedron Letters

Volume

43

Issue

37

Document type

Journal article

Publisher

Elsevier

Topic

  • Chemical Sciences

Keywords

  • solid support
  • antiproliferative
  • xylosides
  • dihydroxynaphthalenes

Status

Published

ISBN/ISSN/Other

  • ISSN: 0040-4039