Synthesis of orthogonally protected 2-deoxystreptamine stereoisomers

Autor:	Tom Wennekes, Jacques H. van Boom, Gijsbert A. van der Marel, Constant A. A. van Boeckel, Herman S. Overkleeft, Steven H. L. Verhelst
Rok vydání:	2004
Předmět:	Allylic rearrangement Chemistry Stereochemistry Organic Chemistry Aminoglycoside Leaving group chemistry.chemical_element General Medicine Metathesis Biochemistry Catalysis Nucleophile Drug Discovery Organic chemistry Amination Palladium
Zdroj:	Tetrahedron. 60:2813-2822
ISSN:	0040-4020
Popis:	Enantiomerically pure 4,6-diaminocyclohexenols are obtained from carbohydrate derived 1,7-dienes by ring-closing metathesis and palladium catalyzed allylic amination using o-nitrobenzenesulfonylamides as nucleophiles. In the latter reaction the use of a cyclic carbonate as a leaving group proved to be essential to facilitate a smooth substitution. The obtained compounds were converted into orthogonally protected diaminocyclitols, which are stereoisomers of the naturally occurring 2-deoxystreptamine, a constituent of aminoglycoside antibiotics.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::20ddf744f0dba854012f1aff5f49c0dd https://doi.org/10.1016/j.tet.2004.01.063 Zobrazit plný text záznamu Full Text from ScienceDirect