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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/1243039
- author
- 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
- organization
- publishing date
- 2008
- 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
- 2024-06-03 19:39:28
@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}},
}