Selective deprotection of tert-butyldimethylsilyl ether with lithium bromide and 18-crown-6

Article abstract of DOI:10.1080/00397919708005001

Lithium bromide, in the presence of a crown ether, has been found to selectively remove primary tert-butyldimethylsilyl ethers under controlled conditions. This selectivity has been utilized to synthesize 3'-TBDMS-2'- deoxyuridine in one step from the diprotected compound.

Full text of DOI:10.1080/00397919708005001

This article was downloaded by: [McGill University Library]
On: 01 January 2013, At: 19:44
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
Selective Deprotection Of
tert-Butyldimethylsilyl Ether
With Lithium Bromide And 18-
Crown-6
Manish Tandon a & Tadhg P. Begley a
a Department of Chemistry, Cornell University,
Ithaca, New York, 14853, U.S.A.
Version of record first published: 22 Aug 2006.
To cite this article: Manish Tandon & Tadhg P. Begley (1997): Selective Deprotection
Of tert-Butyldimethylsilyl Ether With Lithium Bromide And 18-Crown-6, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 27:17, 2953-2959
To link to this article: http://dx.doi.org/10.1080/00397919708005001
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.