949158-97-8Relevant articles and documents
Highly stereoselective and iterative synthesis of α-(1→4)-linked polysaccharides composed of 3-O-methyl-D-mannose
Cheon, Hwan-Sung,Lian, Yiqian,Kishi, Yoshito
, p. 3323 - 3326 (2008/02/13)
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 α-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.