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Synlett 1996; 1996(9): 859-861
DOI: 10.1055/s-1996-5599
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Synthesis of C-Linked Glycosyl Amino Acid Derivatives using Organozinc Reagents

Brian J. Dorgan, Richard F. W. Jackson*
  • *Department of Chemistry, Bedson Building, The University of Newcastle, Newcastle upon Tyne, NE1 7RU, U.K.
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Publication Date:
31 December 2000 (online)

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Reaction of a range of functionalised zinc/copper reagents, including those derived from α-amino acids, with the glucal-derived mesylate 7b leads to a mixture of C-3 and C-1 adducts, in which the former predominates. The stereochemistry of the adducts has been firmly established, and in each case the nucleophile was shown to have attacked from the β-face. By contrast, reaction of the iodohomoalanine-derived zinc reagent 3a with tri-O-acetyl-D-glucal in the presence of boron trifluoride etherate under sonication gives the α-adduct 19 as the major isomer. Conversion of this compound into a protected α-mannosyl C-linked α-amino acid derivative 23 is described.

α-amino acids - organozinc reagents - C-glycosides