246513-15-5Relevant articles and documents
Regiospecific syntheses of N-acetyllactosamine derivatives and application toward a highly practical synthesis of Lewis X trisaccharide
Gan, Zhonghong,Cao, Suoding,Wu, Qingquan,Roy, Rene
, p. 755 - 773 (2007/10/03)
An efficient methodology for regiospecific glycosylation was developed by using 6-O-tert-butyldiphenylsilyl N-acetylglucosamine derivatives 3 and 5 which bear two free hydroxyl groups as acceptors. The regiospecificity was attributed to the presence of the tert-butyldiphenylsilyl group at the O-6 position of the N-acetylglucosamine derivatives. Glycosylation of suitably protected galactoside donors 10-14 with acceptors 3 and 5 gave only β(1→4) linked disaccharides 15-19 in good yields. Fucosylation of disaccharide 18 led to Lewis X (Lex) trisaccharide 21 in high yield.