72263-14-0Relevant academic research and scientific papers
A convenient synthesis of orthogonally protected 2-deoxystreptamine (2-DOS) as an aminocyclitol scaffold for the development of novel aminoglycoside antibiotic derivatives against bacterial resistance
Bauder, Claude
supporting information; experimental part, p. 2952 - 2960 (2009/02/02)
The development of new aminoglycoside analogues to reduce the emergence of bacterial resistance has become a topic of high interest. We describe here a rapid and facile access to orthogonally protected 2-deoxystreptamine (2-DOS), a meso-diaminocyclitol known to be a pivotal component of most active aminoglycosides. Our synthetic approach started from highly protected methyl α-d-glucopyranoside which in turn was converted by a Ferrier rearrangement into an enantiopure polyfunctionalized cyclohexane ring. Finally, two different N-protected groups were successively introduced. The first one was inserted as an oximino benzylether followed by a diastereofacial hydride reduction, working with Me4NBH(OAc)3 only in TFA at low temperature rather than in AcOH as usual. The second group was introduced by displacement of a hydroxyl group through a Mitsunobu reaction using a DPPA-DIAD-Ph3P system for azide transfer. The Royal Society of Chemistry.
THE METHYOXYMERCURATION OF A 6-DEOXYHEX-5-ENOPYRANOSIDE DERIVATIVE AND REACTIONS OF THE PRODUCTS
Ferrier, Robert J.,Prasit, Petpiboon
, p. 263 - 272 (2007/10/02)
Methoxymercuration of methyl 3,4-di-O-benzoyl-6-deoxy-2-O-toluene-p-sulphonyl-α-D-xylo-hex-5-enopyranoside (5) at room temperature with mercury(II) acetate afforded the direct product of addition (8) with mercury bonded to the exocyclic carbon atom.Acetyl
