2-(Trimethylsilyl)ethyl glycosides. Synthesis of the asialo-GM1-tetrasaccharide, spacer glycoside, and BSA and Sepharose glycoconjugates.
The tri and tetra-saccharide glycosides beta-D-GalNAc-(1-4)-beta-D-Gal-(1-4)-beta-D-Glc-1-OTMSEt and beta-D-Gal-(1-3)-beta-D-GalNAc-(1-4)-beta-D-Gal-(1-4)-beta-D-Glc-1-OT MSEt (asialo-GM1) have been synthesized by sequential glycosylations of a suitably protected 2-(trimethylsilyl)ethyl (TMSEt) lactoside with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-galactopyranosyl chloride and 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl bromide. The tetrasaccharide glycoside was transformed into the corresponding hemiacetal sugar as well as the 1-chloro sugar. The latter was used for glycosylation of 2-bromoethanol. The resulting glycoside was used to alkylate methyl 3-mercaptopropionate and the resulting spacer glycoside was used for the preparation of the title glycoconjugates.
Ray
A K
AK
Chemical Center, Lund Institute of Technology, University of Lund, Sweden.
Magnusson
G
G
D002240:Carbohydrate Sequence; D006001:Glycoconjugates / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D012685:Sepharose / Q000737:chemistry*; D012710:Serum Albumin, Bovine / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis*
D006001:Glycoconjugates; D006027:Glycosides; D009844:Oligosaccharides; D014297:Trimethylsilyl Compounds; D012710:Serum Albumin, Bovine; D012685:Sepharose