Practical and scalable synthesis of alpha-(1-->4)-linked polysaccharides composed of 6-O-methyl-D-glucose.
A second-generation synthesis of synthetic 6-O-methyl-D-glucose-containing polysaccharides (sMGPs) is reported. Glycosidation acceptor A and donor B are prepared from alpha-, beta-, and gamma-cyclodextrins in high yields. The glycosidation of A and B, followed by deprotection, furnishes sMGP 12-, 14-, and 16-mers. This synthesis has appealing features such as scalability, operational simplicity, and high overall yield.
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Hwan-Sung
HS
Cheon
Yiqian
Y
Lian
Yoshito
Y
Kishi
D019325:3-O-Methylglucose / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003505:Cyclodextrins / Q000737:chemistry; D006031:Glycosylation; D011134:Polysaccharides / Q000138:chemical synthesis*
D003505:Cyclodextrins; D011134:Polysaccharides; D019325:3-O-Methylglucose