exo-Glycal approaches to C-linked glycosyl amino acid synthesis

Abstract

Two novel routes to C-linked glycosyl amino acids are described; the first involves elaboration of an exo-glycal and subsequent Ramberg–Bäcklund rearrangement of a sulfone intermediate to give, after functional group manipulation, a protected C-glycosyl serine, while the second uses hydroboration–Suzuki coupling of the same exo-glycal to produce ultimately the corresponding C-glycosyl asparagine analogue.

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