Synthesis of new 2-phosphono-alpha-D-glycoside derivatives by stereoselective oxa-Michael addition to a D-galacto derived enone.
The synthesis of new 2-phosphono-alpha-D-glycoside derivatives by stereoselective oxa-Michael addition to an enone derived from D-galactal and containing a phosphonate group is described. Retro-Michael reactions were prevented by tandem acetylation to trap the unstable enolic intermediates. The stereochemistry of the addition products was established by NOESY experiments and explained with molecular mechanics (MM) and density functional theory (DFT) calculations.
Leonelli
Francesca
F
Dipartimento di Chimica, Università La Sapienza, P.le Aldo Moro 5, 00185 Rome, Italy. francesca.leonelli@uniroma1.it
Capuzzi
Marinella
M
Bodo
Enrico
E
Passacantilli
Pietro
P
Piancatelli
Giovanni
G
D000107:Acetylation; D002236:Carbohydrate Conformation; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D006027:Glycosides; C002038:galactal; D005690:Galactose