Synthesis of naphthoxylosides on solid support

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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.

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Nyckelord

Originalspråkengelska
Sidor (från-till)6549-6552
TidskriftTetrahedron Letters
Volym43
Utgivningsnummer37
StatusPublished - 2002
PublikationskategoriForskning
Peer review utfördJa