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Endocyclic cleavage of glycosides. VI. Substituent effects of the alkylative endocyclic cleavage of glycosides

Olsson, Roger LU orcid ; Berg, Ulf LU and Frejd, Torbjörn LU (1998) In Tetrahedron 54(15). p.3935-3954
Abstract


A number of pentopyranoside derivatives were treated with Me
3
Al in order to investigate the influence of structural parameters on the methyl group transfer in the endocyclic alkylative cleavage reaction of these substrates. A cyclic CH ··· O hydrogen bonded model is suggested as an intermediate, which is used to explain the stereoselectivities for different substrates. In several, cases the diastereoselectivities were better than 9:1.

Please use this url to cite or link to this publication:
author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron
volume
54
issue
15
pages
3935 - 3954
publisher
Elsevier
external identifiers
  • scopus:0032499014
ISSN
0040-4020
DOI
10.1016/S0040-4020(98)00120-3
language
English
LU publication?
yes
id
d3e707a7-e3e1-49d1-a153-02f59d60fa99
date added to LUP
2019-10-02 10:52:16
date last changed
2025-10-14 12:33:55
@article{d3e707a7-e3e1-49d1-a153-02f59d60fa99,
  abstract     = {{<p><br>
                            A number of pentopyranoside derivatives were treated with Me<br>
                            <sub>3</sub><br>
                            Al in order to investigate the influence of structural parameters on the methyl group transfer in the endocyclic alkylative cleavage reaction of these substrates. A cyclic CH ··· O hydrogen bonded model is suggested as an intermediate, which is used to explain the stereoselectivities for different substrates. In several, cases the diastereoselectivities were better than 9:1.<br>
                        </p>}},
  author       = {{Olsson, Roger and Berg, Ulf and Frejd, Torbjörn}},
  issn         = {{0040-4020}},
  language     = {{eng}},
  month        = {{04}},
  number       = {{15}},
  pages        = {{3935--3954}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron}},
  title        = {{Endocyclic cleavage of glycosides. VI. Substituent effects of the alkylative endocyclic cleavage of glycosides}},
  url          = {{http://dx.doi.org/10.1016/S0040-4020(98)00120-3}},
  doi          = {{10.1016/S0040-4020(98)00120-3}},
  volume       = {{54}},
  year         = {{1998}},
}