Search results for " C-glycosides"
showing 2 items of 2 documents
Electrochemical synthesis of C-glycosides as non-natural mimetics of biologically active oligosaccharides
2012
Natural oligosaccharides inhibitors of heparanase and selectins are emerging as promising drugs for cancer therapy. As an alternative tool to the natural ones, sulfated tri maltose C-C-linked dimers (alfa,alfa alfa,beta and beta,beta STMCs) were prepared by bromo-maltotriose electroreduction on silver cathode,1 followed by sulfation. The presence of an interglycosidic C-C bond makes STMCs less vulnerable to metabolic processing then their O-analogues. For this reason, STMCs have been studied as drug candidates and inhibitors of carbohydrate processing enzymes. Their activity as inhibitor of Pselectin in vivo and in the attenuation of metastasis both on B16-BL6 melanoma cells and on MC- 38 c…
Diastereoselective synthesis of substituted 2-phenyltetrahydropyrans as useful precursors of aryl C-glycosides via selenoetherification
2004
The cyclization of several substituted 5-phenyl-pent-4-en-1-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.