124662-88-0Relevant articles and documents
Influence of silyl protections on the anomeric reactivity of galactofuranosyl thioglycosides and application of the silylated thiogalactofuranosides to one-pot synthesis of diverse β- D -oligogalactofuranosides
Wang, Shuai,Meng, Xue,Huang, Wei,Yang, Jin-Song
, p. 10203 - 10217 (2014)
We describe in this paper the tuning effect of silyl protecting groups on the donor reactivity of galactofuranosyl phenyl thioglycosides. Silyl ethers on the galactofuranose ring are found to have an arming effect on the glycosylation reactivity, but the cyclic 3,5-acetal protecting group decreases the reactivity. The reactive phenyl 2,6-di-O-Bz-3,5-di-O-TBS-1-thio-β-d-galactofuranoside 3 is proved to be a useful glycosyl building block. By taking advantage of this donor, we achieved the highly efficient one-pot solution-phase assembly of a panel of β-d-galactofuranosyl tri- and tetrasaccharides possessing diverse glycosidic linkages.