Study On The Syntheses And Analysis Of Alkyl 2-deoxyribofuranoside With Protected Groups

A series of alkyl 3,5-di-(O-p-chlorobenzoyl)-2-deoxy ribofunanosides were synthesized and studied. These compounds were obtained from 3,5-di-(O-p-chlorobenzoyl)-D-2-dexoyribosyl chloride and different alcohols as initiative materials in tetrahydrofuran at room temperature.This kinds of compounds were confirmed by their ¹H-NMR, ¹³C-NMR and mass spectrum. Their diasteroisomers were achieved because the group of alkoxy assaulted C₁ of 2-deoxyribofuranosyl chloride from different directions. We selected different eluents according to different diasteroisomers and gained the singles of the diasteroisomers by the column chromatography. At first, the configuration which is a or (3 were judged from its ¹ H-NMR. Secondly, the configuration of the crystal which came from the products of reaction between 3,5-di-O-p-chlorobenzoyl-2-dexoyribosyl chloride and menthol was confirmed. The configuration of crystal is a and the diastereomer is (3, which proved the truth of ¹H-NMR. The configuration of the other diastreoisomers were speculated by the ingredient order from the column chromatography or polarity of them and the speculation is proved to be right by ¹H-NMR. According to two judgements, we marked the spike of the diastreoisomers and provided reliable reference.These diastreoisomers were detected and isolated by HPLC. Taking n-butyl 3,5-di-(O-p-chlorobenzoyl)-α, β-D-2-deoxy ribofunanosides for example, we used the reversed phase liquid chromatographic column of C₁₈ and found the maximum absorbent wavelength making acetonitrile as mobile phase. We selected the normal phase liquid chromatographic column of SiO₂ and used the mixture of n-hexane and isopropanol as the mobile phase. Through adjusting the ratio of the both, we groped for the optimal condition for segregating the diasteroisomers and provided the foundation for analyzing or detecting these anologues.In order to going deep into these kinds of reactions on the basis of the optimal condition of HPLC, the orthogonal experiments were designed which involved time, temperature and solvent of the reaction. The experiments concluded three factors andthree levels of factor. From the consequence of them, we observed the tendency of the condition for the single of (3 or the single of a or the rate of products. These analyses settled the foundation on researching the mechanism or other of this kind of the reactions.