Glycosylation with N-Troc-protected glycosyl donors.
N-Troc-protected (Troc = 2,2,2-trichloroethoxycarbonyl) glucosamine and galactosamine glycosyl donors (1-O-acetyl sugar, bromo sugar, and thioglycoside) were compared with the corresponding N-Phth-protected derivatives in glycosylations of 2-(trimethylsilyl)ethanol, 2-bromoethanol, methyl 3-mercaptopropionate, N-Fmoc-protected serine, and 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside. The N-Troc-protected donors gave pure beta-glycosides in somewhat higher yields than the N-Phth-protected counterparts. The N-Troc protecting group can be removed by reduction with zinc, which allows selective N-deprotection in oligosaccharides containing both N-Troc and N-Phth groups.
Ellervik
U
U
Chemical Center, Lund Institute of Technology, University of Lund, Sweden.
Magnusson
G
G
D002240:Carbohydrate Sequence; D005688:Galactosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013862:Thiogalactosides / Q000737:chemistry; D013863:Thioglucosides / Q000737:chemistry
D006027:Glycosides; D009844:Oligosaccharides; D013862:Thiogalactosides; D013863:Thioglucosides; D005688:Galactosamine; D005944:Glucosamine