Synthesis of C-linked glycopyranosyl serines via a chiral glycine enolate equivalent.
[formula: see text] The stereoselective preparation of C-linked D-gluco- and D-galactopyranosyl L-serines in their alpha and beta forms is herein reported. The syntheses require the conversion of the allyl C-glycopyranosides into their iodoethyl derivatives, which then undergo substitution with the Williams' chiral glycine enolate equivalent. Deprotection and acetylation affords Boc-protected amino acids for peptide synthesis.
Nolen
Ernest G
EG
Department of Chemistry, Colgate University, Hamilton, New York 13346, USA. enolen@mail.colgate.edu
Watts
Micah M
MM
Fowler
Daniel J
DJ
D000478:Alkylation; D005697:Galactosides / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis; D006020:Glycopeptides / Q000138:chemical synthesis; D006027:Glycosides; D009005:Monosaccharides / Q000138:chemical synthesis*; D012694:Serine / Q000138:chemical synthesis*
C438934:C-glycoside; D005697:Galactosides; D005960:Glucosides; D006001:Glycoconjugates; D006020:Glycopeptides; D006027:Glycosides; D009005:Monosaccharides; C405611:glycine enol; D012694:Serine; D005998:Glycine