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Stereospecific Synthesis of the Saccharosamine-Rhamnose-Fucose Fragment Present in Saccharomicin B

July 17, 2018

Marissa Bylsma and Clay S. Bennett
Organic Letters, 2018, 20 (15), pp 4695–4698 DOI: 10.1021/acs.orglett.8b02028


A synthetic route has been developed for constructing the d-saccharosamine-l-rhamnose-d-fucose (Sac-Rha-Fuc) trisaccharide fragment present in the antibacterial natural product saccharomicin B. The Sac monosaccharide was synthesized through a modified nine step procedure starting from d-rhamnal in 23% overall yield. 1-O-TBS Sac donors were used to construct the β-linked Sac-Rha disaccharide. This disaccharide was coupled to a Fuc acceptor under BSP/Tf2O conditions to afford a trisaccharide properly functionalized for elaboration to saccharomicin B.


Source: https://pubs.acs.org/doi/10.1021/acs.orglett.8b02028