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Chelation-controlled regioselective endo cleavage and stereoselective C-1 alkylation of pentofuranosides

Olsson, Roger LU ; Rundström, Pontus and Frejd, Torbjörn LU (1998) In Journal of the Chemical Society - Perkin Transactions 1 p.785-790
Abstract

Combinations of Lewis acids and nucleophilic reagents trigger endo-opening of the furanoside ring of methyl furanosides 1, 10 and 13, resulting in the attachment of the nucleophilic group at C-1 of the carbohydrate. The stereoselectivity in the C-C bond-forming step is low for the 2-deoxyfuranosides but very high (dr 1:99) for the furanosides carrying a methoxy group in the 2-position when a combination of TiCl4 and Me2Zn is used. Different selectivities are obtained with Me2Zn as compared with Me3Al. Reagents based on several organometallic reagents of Al, Si, Ti and Zn in combination with TiCl4 can be used.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of the Chemical Society - Perkin Transactions 1
issue
4
pages
785 - 790
external identifiers
  • scopus:33745689669
ISSN
0300-922X
DOI
10.1039/a706166h
language
English
LU publication?
yes
id
bd47e67d-2735-4f74-996d-ec0b73055397
date added to LUP
2019-10-02 10:51:19
date last changed
2020-01-13 02:26:21
@article{bd47e67d-2735-4f74-996d-ec0b73055397,
  abstract     = {<p>Combinations of Lewis acids and nucleophilic reagents trigger endo-opening of the furanoside ring of methyl furanosides 1, 10 and 13, resulting in the attachment of the nucleophilic group at C-1 of the carbohydrate. The stereoselectivity in the C-C bond-forming step is low for the 2-deoxyfuranosides but very high (dr 1:99) for the furanosides carrying a methoxy group in the 2-position when a combination of TiCl<sub>4</sub> and Me<sub>2</sub>Zn is used. Different selectivities are obtained with Me<sub>2</sub>Zn as compared with Me<sub>3</sub>Al. Reagents based on several organometallic reagents of Al, Si, Ti and Zn in combination with TiCl<sub>4</sub> can be used.</p>},
  author       = {Olsson, Roger and Rundström, Pontus and Frejd, Torbjörn},
  issn         = {0300-922X},
  language     = {eng},
  month        = {02},
  number       = {4},
  pages        = {785--790},
  series       = {Journal of the Chemical Society - Perkin Transactions 1},
  title        = {Chelation-controlled regioselective endo cleavage and stereoselective C-1 alkylation of pentofuranosides},
  url          = {http://dx.doi.org/10.1039/a706166h},
  doi          = {10.1039/a706166h},
  year         = {1998},
}