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Synthesis 2007(22): 3589-3594
DOI: 10.1055/s-2007-990858
DOI: 10.1055/s-2007-990858
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Synthesis of a 5-Spirocyclopropyl Deoxyrhamnojirimycin as a Constrained Naringinase Inhibitor
Further Information
Received
19 July 2007
Publication Date:
29 October 2007 (online)
Publication History
Publication Date:
29 October 2007 (online)
Abstract
A spirocyclopropyl analogue of deoxyrhamnojirimycin has been synthesized in 11 steps and 20% overall yield from l-arabinose. The key step of the reaction path involves titanium-mediated aminocyclopropanation of an l-arabinononitrile derivative. Improvements of the standard reaction conditions were investigated. The use of methyltitanium triisopropoxide as the titanium source allowed the reaction to take place at room temperature and afforded the corresponding cyclopropylamine in 80% yield.
Key words
glycosidases - imino sugars - metallacycles - nitriles - spiro compounds - titanium
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