Highly stereoselective and iterative synthesis of alpha-(1-->4)-linked polysaccharides composed of 3-O-methyl-D-mannose.
A second-generation synthesis of synthetic 3-O-methyl-D-mannose-containing polysaccharides (sMMPs) is reported. The glycosidation of donor B and acceptor C, prepared from a common precursor A in two and one steps, respectively, is effected by t-butyldimethylsilyl trifluoromethanesulfonate to furnish only the desired alpha-anomer D in high yields. Unlike the first-generation synthesis, this synthesis gives the desired product free from contamination of scrambling products. A three-step protocol is used to deprotect D to furnish sMMPs.
Cheon
Hwan-Sung
HS
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Lian
Yiqian
Y
Kishi
Yoshito
Y
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006031:Glycosylation; D008766:Methylmannosides / Q000737:chemistry*; D011134:Polysaccharides / Q000138:chemical synthesis*
D008766:Methylmannosides; D011134:Polysaccharides; C043123:3-O-methylmannose