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HERO ID
618416
Reference Type
Journal Article
Title
Optimized synthesis of LNA uracil nucleosides
Author(s)
Kumar, ST; Kumar, P; Sharma, PK; Hrdlicka, PJ
Year
2008
Is Peer Reviewed?
1
Journal
Tetrahedron Letters
ISSN:
0040-4039
EISSN:
1873-3581
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Location
OXFORD
Volume
49
Issue
50
Page Numbers
7168-7170
DOI
10.1016/j.tetlet.2008.09.165
Web of Science Id
WOS:000261230100021
URL
http://linkinghub.elsevier.com/retrieve/pii/S0040403908018583
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Abstract
Abstract: A short, very high yielding, and practical synthesis of LNA uracil diol 6 has been developed from the easily accessible glycosyl donor 1. The concluding O3′-debenzylation of 5 resulted in significant reduction of the uracil moiety with many typical debenzylation conditions, while catalytic transfer hydrogenation using Pd(OH)2/C and formic acid largely suppressed this undesired side reaction. Facile access to 6 will allow full exploration of RNA-based LNA-technology applications, including polymerase-catalyzed synthesis of LNA-modified RNA-strands. [Copyright 2008 Elsevier] Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts)
Keywords
NUCLEOSIDES; HETEROCYCLIC compounds; URACIL; CHEMICAL reactions; FORMIC acid; HYDROGENATION
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