Syntheses of alpha- and beta-C-glucopyranosyl serines from a common intermediate.
A versatile synthesis leading to either C-linked alpha- or beta-glucopyranosyl serines is presented from a common, advanced synthetic intermediate. Cyclization of the penultimate carbinol onto the alkene and methanolysis of the lactone yields selectively the alpha-linkage. A transposition of these last steps leads to the beta-linked isomer selectively.
Nolen
Ernest G
EG
Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York 13346, USA. enolen@colgate.edu
Donahue
Laurence A
LA
Greaves
Rebecca
R
Daly
Trevor A
TA
Calabrese
David R
DR
D003500:Cyclization; D004951:Esterification; D005947:Glucose / Q000737:chemistry*; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D012694:Serine; D005947:Glucose