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  • A short and highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides.

A short and highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides.

Organic letters (2011-01-20)
Feiqing Ding, Ronny William, Fei Wang, Jimei Ma, Li Ji, Xue-Wei Liu
PMID21244045
ABSTRACT

A highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides via BF(3)·OEt(2) promoted tandem hydroamination/glycosylation of 3,4-di-O-acetyl-6-deoxy-L-glucal and L-galactal has been developed. The new method proceeds in a completely stereocontrolled manner within a short reaction time. Preparation of a library of L-ristosamine and L-epi-daunosamine glycosides with potential biochemical applications, by varying each component, exemplified the generality of the reaction.