Synthesis of a C-glycoside analogue of beta-D-galactosyl hydroxynorvaline and its use in immunological studies.

@article{Wellner2000SynthesisOA,
  title={Synthesis of a C-glycoside analogue of beta-D-galactosyl hydroxynorvaline and its use in immunological studies.},
  author={Erik Wellner and Tomas Gustafsson and Johan B{\"a}cklund and Rikard Holmdahl and Jan Kihlberg},
  journal={Chembiochem : a European journal of chemical biology},
  year={2000},
  volume={1 4},
  pages={272-80}
}
A C-linked isostere of beta-D-galactosylated hydroxynorvaline has been prepared in eight steps from per-O-benzylated galactopyranolactone. Addition of a homoallylic Grignard reagent to the lactone, reduction of the resulting hemiacetal with triethylsilane, and a Wittig reaction with Garner's aldehyde were key steps in this synthesis. The C-linked building… CONTINUE READING