72263-10-6Relevant articles and documents
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.
Unsaturated Carbohydrates. Part 28. Observations on the Conversion of 6-Deoxyhex-5-enopyranosyl Compounds into 2-Deoxyinosose Derivatives
Blattner, Regine,Ferrier, Robert J.,Haines, Stephen R.
, p. 2413 - 2416 (2007/10/02)
Mercury-containing intermediates have been isolated from the reaction of 6-deoxyhex-5-enopyranosyl compounds with mercury(II) salts in aqueous acetone.They react to give 2-deoxyinosose derivatives on further exposure to the conditions of their formation o
