Synthesis of naphthoxylosides on solid support
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/329335
- author
- Jacobsson, Mårten LU and Ellervik, Ulf LU
- organization
- publishing date
- 2002
- 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
- 2024-01-10 23:31:51
@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}}, keywords = {{solid support; antiproliferative; xylosides; dihydroxynaphthalenes}}, 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}}, }