Alternative syntheses of L-(-)-oleandrose from L-rhamnose. Preparation of glycals

Article abstract of DOI:10.1080/00397919208021642

L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oleandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl α-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).

Full text of DOI:10.1080/00397919208021642

This article was downloaded by: [North Carolina State University]
On: 29 November 2012, At: 19:43
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
Alternative Syntheses of L-(-)-
Oleandrose from L-Rhamnose1
Preparation of Glycals
Martin W. Bredenkamp a , Cedric W. Holzapfel a &
Francois Toerien a
a Department of Chemistry and Biochemistry, Rand
Afrikaans University, P.O. Box 524, Aucklandpark
2006, Johannesburg, South Africa
Version of record first published: 23 Sep 2006.
To cite this article: Martin W. Bredenkamp, Cedric W. Holzapfel & Francois Toerien
(1992): Alternative Syntheses of L-(-)-Oleandrose from L-Rhamnose1 Preparation of
Glycals, Synthetic Communications: An International Journal for Rapid Communication
of Synthetic Organic Chemistry, 22:17, 2459-2477
To link to this article: http://dx.doi.org/10.1080/00397919208021642
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/terms-
and-conditions
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden.

The publisher does not give any warranty express or implied or make any
representation that the contents will be complete or accurate or up to
date. The accuracy of any instructions, formulae, and drug doses should be
independently verified with primary sources. The publisher shall not be liable
for any loss, actions, claims, proceedings, demand, or costs or damages
whatsoever or howsoever caused arising directly or indirectly in connection
with or arising out of the use of this material.