Chelation-controlled regioselective endo cleavage and stereoselective C-1 alkylation of pentofuranosides
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/bd47e67d-2735-4f74-996d-ec0b73055397
- author
- Olsson, Roger LU ; Rundström, Pontus and Frejd, Torbjörn LU
- organization
- publishing date
- 1998-02-21
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Journal of the Chemical Society - Perkin Transactions 1
- issue
- 4
- pages
- 785 - 790
- publisher
- Royal Society of Chemistry
- 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
- 2022-07-19 23:54:37
@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}}, publisher = {{Royal Society of Chemistry}}, 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}}, }