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Regioselective reductive openings of acetals; Mechanistic details and synthesis of fluorescently labeled compounds

Johnsson, Richard LU ; Mani, Katrin LU ; Cheng, Fang LU and Ellervik, Ulf LU (2006) In Journal of Organic Chemistry 71(9). p.3444-3451
Abstract
Regioselective reductive openings of mixed phenolic-benzylic acetals, using BH3 center dot NMe3 center dot AlCl3, was investigated, and a mechanism where the outcome is directed by the electrostatic potential of the two oxygen atoms is presented. The regioselective acetal opening was used in the synthesis of a fluorescently labeled analogue to antiproliferative xylosides. The fluorescently labeled xyloside was tested for uptake, anti proliferative activity, and glycosaminoglycan priming in different cell lines. The xyloside was taken up by all cell lines but did not initiate glycosaminoglycan biosynthesis.
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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
71
issue
9
pages
3444 - 3451
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000237027000015
  • scopus:33646261669
ISSN
1520-6904
DOI
10.1021/jo0526284
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: Organic chemistry (S/LTH) (011001240), Glycobiology (013212006)
id
815c7b30-5f13-442c-84e3-0dc8df96a35a (old id 410698)
date added to LUP
2016-04-01 11:35:28
date last changed
2021-10-06 05:23:18
@article{815c7b30-5f13-442c-84e3-0dc8df96a35a,
  abstract     = {Regioselective reductive openings of mixed phenolic-benzylic acetals, using BH3 center dot NMe3 center dot AlCl3, was investigated, and a mechanism where the outcome is directed by the electrostatic potential of the two oxygen atoms is presented. The regioselective acetal opening was used in the synthesis of a fluorescently labeled analogue to antiproliferative xylosides. The fluorescently labeled xyloside was tested for uptake, anti proliferative activity, and glycosaminoglycan priming in different cell lines. The xyloside was taken up by all cell lines but did not initiate glycosaminoglycan biosynthesis.},
  author       = {Johnsson, Richard and Mani, Katrin and Cheng, Fang and Ellervik, Ulf},
  issn         = {1520-6904},
  language     = {eng},
  number       = {9},
  pages        = {3444--3451},
  publisher    = {The American Chemical Society (ACS)},
  series       = {Journal of Organic Chemistry},
  title        = {Regioselective reductive openings of acetals; Mechanistic details and synthesis of fluorescently labeled compounds},
  url          = {http://dx.doi.org/10.1021/jo0526284},
  doi          = {10.1021/jo0526284},
  volume       = {71},
  year         = {2006},
}