Synthesis Of 5-Thio-L-Idose And Thioglycosides

Thiosugars include a series of compounds with substitution of the oxygen ring atom of pyranosides or furanosides by a sulfur atom and thioglycosides. Thiosugars with a sulfur atom in the ring have been found in Nature and, as for many of the synthetic thiosugars with a sulfur atom in the ring, display interesting biological activities. According to available literatures, with anhydrous glucose as the starting-material, synthetic routes of 5-thio-L-idopyranoside had been improved and the yield rose. We cultivated crystal of a series of intermediates and found some mistakes in these literatures.Thioglycosides have found their place in carbohydrate chemistry and carbohydrate biology as an important tool. Natural coumarin compounds have important biological and pharmacological activities, Such as: anti-hypertensive, anti-coagulation, anti-fungal, anti-bacterial, hypoglycemic, anti-virus and anti-cancer and so on. Particularly, certain derivatives have anti-HIV activity and anti-tumor activity. Thus, scholars both domestic and foreign pay more attention to this study. In view of this, we use peracetyl glycosylthiols and bromomethylcoumarins to afford a series of novel compounds. The structures of all the synthesized compounds were confirmed by IR, 1H NMR spectral date and elemental analysis.The major works of this thesis:1. With anhydrous glucose as the starting-material, synthetic routes of 5-thio-L-idopyranoside had been improved and the yield rose.2. By the reaction of bromomethylcoumarins with peracetyl glycosylthiols, a series of novel thioglycosides were produced.The Innovations of the Thesis:1 Improve the synthetic routes of 5-thio-L-idopyranoside.2 Crystal structures of a series of intermediates proved some mistakes of the literatures.3 A series of novel thioglycosides were obtained by SN2 displacement reactions of bromomethylcoumarin with peracetyl glycosylthiols triumphantly, and they may be provided with some biological activities.