Synthesis of a protected enantiomerically pure 2-deoxystreptamine derivative from D-allylglycine
Publication year
2004Source
Tetrahedron Letters, 45, 18, (2004), pp. 3629-3632ISSN
Publication type
Article / Letter to editor
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Organization
Synthetic Organic Chemistry
Journal title
Tetrahedron Letters
Volume
vol. 45
Issue
iss. 18
Page start
p. 3629
Page end
p. 3632
Subject
Synthetic Organic ChemistryAbstract
A diastereoselective synthetic route from D-allylglycine to the enantiopure (protected) 2-deoxystreptamine derivative 14 is presented. Key steps involve two consecutive chain extensions-with crucial stereodirective roles for the amino protective groups, ring closure by olefin metathesis, face selective dihydroxylation, cyclic sulfate formation and finally opening with azide. The resulting 2-deoxystreptamine derivative is ideally protected for the preparation of 4,5- or 4,6-linked aminoglycoside antibiotics. (C) 2004 Elsevier Ltd. All rights reserved.
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