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Synthesis of naphthoxylosides on solid support

Jacobsson, Mårten LU and Ellervik, Ulf LU (2002) In Tetrahedron Letters 43(37). p.6549-6552
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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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
solid support, antiproliferative, xylosides, dihydroxynaphthalenes
in
Tetrahedron Letters
volume
43
issue
37
pages
6549 - 6552
publisher
Elsevier
external identifiers
  • wos:000177659700013
  • scopus:0037048458
ISSN
0040-4039
DOI
10.1016/S0040-4039(02)01467-3
language
English
LU publication?
yes
additional info
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)
id
3222c0d4-07fb-4d58-926a-bbf801ab1c8a (old id 329335)
date added to LUP
2016-04-01 15:59:32
date last changed
2020-01-12 18:55:58
@article{3222c0d4-07fb-4d58-926a-bbf801ab1c8a,
  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.},
  author       = {Jacobsson, Mårten and Ellervik, Ulf},
  issn         = {0040-4039},
  language     = {eng},
  number       = {37},
  pages        = {6549--6552},
  publisher    = {Elsevier},
  series       = {Tetrahedron Letters},
  title        = {Synthesis of naphthoxylosides on solid support},
  url          = {http://dx.doi.org/10.1016/S0040-4039(02)01467-3},
  doi          = {10.1016/S0040-4039(02)01467-3},
  volume       = {43},
  year         = {2002},
}