Practical synthesis of the disaccharide epitope, D-galactopyranosyl-alpha-1,3-D-galactopyranose, by using 1,2;5,6-di-O-cyclohexylidene-alpha-D-galactofuranose as the glycosyl acceptor.
D-Galactosyl-alpha-1,3-D-galactopyranose (1) was chemically prepared in a good yield by coupling phenyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside (5) or 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl bromide (8) with 1,2:5,6-di-O-cyclohexylidene-alpha-D-galactofuranose (3) with subsequent de-O-benzylation and de-O-cyclohexylidenation of the resulting protected alpha1,3-disaccharide.
Sakamoto
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I
Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Ohrui
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H
D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D000939:Epitopes / Q000737:chemistry*; D005690:Galactose / Q000031:analogs & derivatives*; D007202:Indicators and Reagents; D008958:Models, Molecular
C419925:1,2-5,6-di-O-cyclohexylidene-galactofuranose; D004187:Disaccharides; D000939:Epitopes; D007202:Indicators and Reagents; C055075:galactosyl-(1-3)galactose; D005690:Galactose