96711-93-2

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.

A synthesis of the naturally occurring inhibitor of chitin metabolism, allosamidin 1, involves, as the key step, condensation between the allosamizoline derivative 39, prepared following oxyamination of the cyclopentene 19, and the disaccharide glycosylating agent 54 which was synthesised from 2-acetamido-2-deoxy-D-glucose.The structural isomer 59 of allosamidin is also reported.Brief biological test results obtained using isomers 1 and 59 are recorded.