Synthesis of new di-1, 2, 3-Triazoline derivatives for D-3-deoxy-Ribohexulose sugar derivative

Abstract

To achieve this work, Methyl- D- fructpyranoside (1) was synthesized first by treating D-Fructose with Methanol in acidic medium under thermodynamically controlled conditions to make sure that the fructopyranoside are the predominant product. The hydroxyl group at C₄ and C₅ were converted into Isopropylidine (2) by treating (1) with Acetone in acidic medium, and hydroxyl group on C₁ and C₃ were converted into mesylester (3) by treated (2) with two equivalents of mesylchloride at 0C^º. The vital compound in this synthesis compound (4) was obtained by treatment of (3) with two moles of sodiumazide in presence of TBAB. Reaction (4) with unsaturated compound like maleicanhydride, p-benzoquinone, cinnamylalcohol, acrylamide, benzalacetophenone and vinylacetate formed compounds (5), (6), (7), (8), (9) and (10) respectively. The course of the reactions as well as the purity of products were monitored by means of T.L.C.  Identification of products were achieved by elemental analysis (C.H.N), I.R. spectroscopy and ¹HN.M.R.