Synthesis of naphthoxylosides on solid support

Mårten Jacobsson, Ulf Ellervik

Research output: Contribution to journalArticlepeer-review

13 Citations (SciVal)

Abstract

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.
Original languageEnglish
Pages (from-to)6549-6552
JournalTetrahedron Letters
Volume43
Issue number37
DOIs
Publication statusPublished - 2002

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Center for Chemistry and Chemical Engineering (011001000), Organic chemistry (S/LTH) (011001240), Centre for Analysis and Synthesis (011001266)

Subject classification (UKÄ)

  • Chemical Sciences

Keywords

  • solid support
  • antiproliferative
  • xylosides
  • dihydroxynaphthalenes

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