Mono- and Di-Sulfonate Esters of ？-L-Arabinochloralose; 3-O-Protected-5-Azido and 5-O-Alkyl Derivatives

In this research, it was aimed to synthesize the organic compounds containing di-mesylate (methane sulfonate) and di-tosylate ester groups on the simple monosaccharide skeleton and mono-mesylate and mono-tosylate organic derivatives including azido groups in the primer position. In this target, β-L-arabinofuranose was chosen as the starting sugar. After the reaction of this monosaccharide unit with chloral in the presence of concentrated H2SO4, 1,2-O-(S)-trichloroethylidene-β-L-arabinofuranose was firstly obtained. The ester derivatives, 3,5-di-O-mesyl (di-mesylate) and 3,5-di-O-tosyl (di-tosylate), were then synthesized on this sugar skeleton protected with trichloroethylidene acetal ring. 5-Azido-3-O-mesyl and 5-azido-3-O-tosyl derivatives of these di-mesylate and di-tosylate ester derivatives were subsequently obtained under appropriate reaction conditions. Furthermore, the mono-tosylate ester derivative of 1,2-O-(S)-Trichloroethylidene-β-L-arabinofuranose was reacted with methyl iodide in the presence of silver oxide to obtain the corresponding 5-O-tosil-3-O-methyl derivative. This obtained derivative was converted to the 5-Azido-3-O-methyl derivative under suitable reaction conditions. In addition, the 1,2-O-(S)-Trichloroethylidene-β-L-arabinofuranose was reacted with trityl chloride to produce the corresponding 5-O-trityl derivative. The 5-O-Trityl-3-O-methyl arabinochloralose was synthesized by the methylation reaction of 5-O-trityl derivative. Thus, the secondary hydroxyl group of the carbohydrate skeleton unit is protected by methyl group in the 5-O-tosyl and 5-O-trityl derivatives. All newly synthesized molecules were structurally characterized by using spectroscopic techniques (IR, NMR and Mass)