Synthesis of beta-C-galacto-pyranosides with fluorine on the pseudoanomeric substituent.
[reaction: see text] beta-C-galacto-Pyranosides with CHF and CF2 substitutes for the glycosidic oxygen were prepared through a four-step sequence starting from a central 1-thio-1,2-O-isopropylidene acetal alcohol and different alpha-fluoro- and alpha,alpha-difluoro acids. The key step in the synthesis is the oxocarbenium cyclization of an intermediate enol ether-thioacetal to a C1-substituted glycal.
Tony
Kurissery A
KA
Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10021, USA.
Denton
Richard W
RW
Dilhas
Anna
A
Jiménez-Barbero
Jesús
J
Mootoo
David R
DR
D000143:Acids / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D005690:Galactose / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D015394:Molecular Structure
D000143:Acids; D006027:Glycosides; D005461:Fluorine; D005690:Galactose