New stereoselective beta-C-glycosidation by uncatalyzed 1,4-addition of organolithium reagents to a glycal-derived vinyl oxirane.
[reaction: see text] Epoxide 4 is generated in situ from d-glucal-derived hydroxy mesylate 3. Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents affords 2,3-unsaturated beta-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivity for the beta-glycoside. Other organometallic reagents demonstrate more complex behavior in their reactions with epoxide 4.
Di Bussolo
Valeria
V
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy.
Caselli
Micaela
M
Pineschi
Mauro
M
Crotti
Paolo
P
D005027:Ethylene Oxide / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D005960:Glucosides; D009942:Organometallic Compounds; D008094:Lithium; D005027:Ethylene Oxide