Highly efficient and stereoselective synthesis of beta-glycolipids.
beta-Galactosylceramide and glycolipid analogues were prepared in high yield and with complete chemo and stereoselectivity by reaction of alpha-iodo glycosides with stannyl ceramides, formed in situ. TBAI was used to activate both the iodogalactose and the stannyl ether.
Morales-Serna
José Antonio
JA
Departamento de Química Analítica y Química Orgánica, Universitat Rovira i Virgili, C/Marcel.li Domingo s/n, 43007 Tarragona, Spain.
Boutureira
Omar
O
Díaz
Yolanda
Y
Matheu
M Isabel
MI
Castillón
Sergio
S
D002518:Ceramides / Q000138:chemical synthesis / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D002518:Ceramides; D006017:Glycolipids; D009005:Monosaccharides; C511581:beta-galactosyl ceramide