Synthesis of 5'-fluoro-5'-deoxy- and 5'-amino-5'-deoxytoyocamycin and sangivamycin and some related derivatives

Article abstract of DOI:10.1080/15257779508010707

A series of 5'-substituted analogs of toyocamycin were prepared by condensation of silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with protected 5-azido-5-deoxy- or 5-fluoro-5-deoxyribofuranose followed by debromination and deblocking. Alternatively, 5'-azido-5'-deoxytoyocamycin was prepared by azidation of toyocamycin. Conversion of the 5-nitrile function of the toyocamycin derivatives into a carboxamide or a thiocarboxamide gave the corresponding analogs of sangivamycin or thiosangivamycin while reduction of the 5'-azido-5'-deoxy nucleosides provided 5'-amino-5'-deoxy derivatives.

Full text of DOI:10.1080/15257779508010707

This article was downloaded by: ["Queen's University Libraries, Kingston"]
On: 02 February 2015, At: 13:23
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
Nucleosides and Nucleotides
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/lncn19
Synthesis of 5′-Fluoro-5′-deoxy-
and 5′-Amino-5′-Deoxytoyocamycin
and Sangivamycin and Some Related
Derivatives
Moheshwar Sharma a , Yi X. Li a , Miroslav Ledvina a & Miroslav
Bobek a
a Grace Cancer Drug Center, Roswell Park Cancer Institute , Elm
and Carlton Streets, Buffalo, New York, 14263, U.S.A.
Published online: 24 Sep 2006.
To cite this article: Moheshwar Sharma , Yi X. Li , Miroslav Ledvina & Miroslav Bobek (1995)
Synthesis of 5′-Fluoro-5′-deoxy-and 5′-Amino-5′-Deoxytoyocamycin and Sangivamycin
and Some Related Derivatives, Nucleosides and Nucleotides, 14:9-10, 1831-1852, DOI:
10.1080/15257779508010707
To link to this article: http://dx.doi.org/10.1080/15257779508010707
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the
“Content”) contained in the publications on our platform. However, Taylor & Francis,
our agents, and our licensors make no representations or warranties whatsoever as to
the accuracy, completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims,
proceedings, demands, costs, expenses, damages, and other liabilities whatsoever
or howsoever caused arising directly or indirectly in connection with, in relation to or
arising out of the use of the Content.
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. Terms
& Conditions of access and use can be found at http://www.tandfonline.com/page/
terms-and-conditions