Action of base on methyl 6-thio-(and 6-deoxy-) 2-O-methanesulfonyl-α-D-glucopyranoside derivatives

Article abstract of DOI:10.1080/07328309808005769

Treatment of methyl 4-O-benzoyl-3 -O-tert-butyldiphenylsilyl-2-O-methanesulfonyl-6-thio-α-D-glucopyranoside (8) and its 6-deoxy analogue (11) with methanolic sodium methoxide, afforded methyl 2,3-anhydro-mannopyranoside derivatives as a consequence of an O₃ → O₄ TBDPS rearrangement. When the protecting group at C-3 was 2-methoxyethoxy methyl ether only deacylation and methanolysis of the methanesulfonyl group occurred.

Full text of DOI:10.1080/07328309808005769

This article was downloaded by: [Moskow State Univ Bibliote]
On: 13 December 2013, At: 23:14
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
Journal of Carbohydrate Chemistry
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/lcar20
Action of Base on Methyl 6-Thio- (and
6-Deoxy-) 2-O-Methanesulfonyl-α-d-
Glucopyranoside Derivatives1
Isidoro Izquierdo a , Miguel Rodríguez a , María T. Plaza a & Julia
Pleguezuelos a
a Department of Organic Chemistry , Faculty of Pharmacy University
of Granada , E-18071, Granada, Spain
Published online: 16 Aug 2006.
To cite this article: Isidoro Izquierdo , Miguel Rodríguez , María T. Plaza & Julia Pleguezuelos
(1998) Action of Base on Methyl 6-Thio- (and 6-Deoxy-) 2-O-Methanesulfonyl-α-d-Glucopyranoside
Derivatives1 , Journal of Carbohydrate Chemistry, 17:1, 61-74, DOI: 10.1080/07328309808005769
To link to this article: http://dx.doi.org/10.1080/07328309808005769
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