Jump to main content
Jump to site search

Issue 16, 2008
Previous Article Next Article

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

Author affiliations

Abstract

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.

Graphical abstract: 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

Back to tab navigation

Supplementary files

Publication details

The article was received on 20 Mar 2008, accepted on 19 May 2008 and first published on 20 Jun 2008


Article type: Paper
DOI: 10.1039/B804784G
Citation: Org. Biomol. Chem., 2008,6, 2952-2960
  •   Request permissions

    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

    C. Bauder, Org. Biomol. Chem., 2008, 6, 2952
    DOI: 10.1039/B804784G

Search articles by author

Spotlight

Advertisements