688334-43-2Relevant academic research and scientific papers
Synthesis of orthogonally protected 2-deoxystreptamine stereoisomers
Verhelst, Steven H.L.,Wennekes, Tom,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Van Boeckel, Constant A.A.,Van Boom, Jacques H.
, p. 2813 - 2822 (2007/10/03)
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.
