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Synthesis of the Non-Reducing Hexasaccharide Fragment of Saccharomicin B

November 14, 2018

ACS Publications, Organic Letters, 2018 Nov 14. doi: 10.1021/acs.orglett.8b03333
Manas Jana and Clay S. Bennett


A synthesis of the nonreducing end hexasaccharide of saccharomicin B, α-l-Eva-(1→4)-α-l-Eva-(1→4)-α-l-Dig-(1→4)-α-l-Eva-(1→4)-α-l-Dig-(1→4)-β-d-Fuc, has been developed. Selective glycosylations of l-digitoxose (l-Dig) using AgPF6/TTBP-mediated thioether activation and l-4-epi-vancosamine (l-Eva) using Tf2O/DTBMP-mediated sulfoxide activation produced the hexasaccharide as a single diastereomer in very good yield. This hexasaccharide is properly functionalized to serve as a glycosyl donor for the total synthesis of saccharomicin B.


Source: https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.8b03333