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Reductive openings of benzylidene acetals. Kinetic studies of borane and alane activation by Lewis acids.

Johnsson, Richard LU ; Cukalevski, Risto ; Dragén, Fanny LU ; Ivanisevic, Damir ; Johansson, Ida ; Petersson, Linn LU ; Elgstrand Wettergren, Erika ; Yam, Ka Bo ; Yang, Beatrice and Ellervik, Ulf LU (2008) In Carbohydrate Research 343. p.2997-3000
Abstract
The reaction kinetics for a number of reductive openings of methyl 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-d-glucopyranoside have been investigated. Openings to give free HO-6 (using BH(3).THF-AlCl(3)-THF or LiAlH(4)-AlCl(3)-Et(2)O) follow first order kinetics, while reactions yielding free HO-4 (using BH(3).NMe(3)-AlCl(3)-THF or BH(3).NMe(3)-BF(3).OEt(2)-THF) follow higher order kinetics. The addition of water to the BH(3).NMe(3)-AlCl(3)-THF results in faster reactions. The BH(3).SMe(2)-AlCl(3)-THF system constitutes a borderline case, yielding both free HO-6 (by a first order reaction) and free HO-4 (by a higher order reaction). These results correlate well with the concept of regioselectivity by activation of borane complexes.
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author
; ; ; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Carbohydrate Research
volume
343
pages
2997 - 3000
publisher
Elsevier
external identifiers
  • pmid:18789434
  • wos:000261134300020
  • scopus:53849132333
  • pmid:18789434
ISSN
1873-426X
DOI
10.1016/j.carres.2008.08.022
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: Department of Immunotechnology (011029300), Organic chemistry (S/LTH) (011001240)
id
89ae571f-9202-43fe-a96d-b8e323cd73e9 (old id 1243039)
date added to LUP
2016-04-01 11:46:16
date last changed
2022-02-25 21:08:00
@article{89ae571f-9202-43fe-a96d-b8e323cd73e9,
  abstract     = {{The reaction kinetics for a number of reductive openings of methyl 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-d-glucopyranoside have been investigated. Openings to give free HO-6 (using BH(3).THF-AlCl(3)-THF or LiAlH(4)-AlCl(3)-Et(2)O) follow first order kinetics, while reactions yielding free HO-4 (using BH(3).NMe(3)-AlCl(3)-THF or BH(3).NMe(3)-BF(3).OEt(2)-THF) follow higher order kinetics. The addition of water to the BH(3).NMe(3)-AlCl(3)-THF results in faster reactions. The BH(3).SMe(2)-AlCl(3)-THF system constitutes a borderline case, yielding both free HO-6 (by a first order reaction) and free HO-4 (by a higher order reaction). These results correlate well with the concept of regioselectivity by activation of borane complexes.}},
  author       = {{Johnsson, Richard and Cukalevski, Risto and Dragén, Fanny and Ivanisevic, Damir and Johansson, Ida and Petersson, Linn and Elgstrand Wettergren, Erika and Yam, Ka Bo and Yang, Beatrice and Ellervik, Ulf}},
  issn         = {{1873-426X}},
  language     = {{eng}},
  pages        = {{2997--3000}},
  publisher    = {{Elsevier}},
  series       = {{Carbohydrate Research}},
  title        = {{Reductive openings of benzylidene acetals. Kinetic studies of borane and alane activation by Lewis acids.}},
  url          = {{http://dx.doi.org/10.1016/j.carres.2008.08.022}},
  doi          = {{10.1016/j.carres.2008.08.022}},
  volume       = {{343}},
  year         = {{2008}},
}