| Summary: | 碩士 === 輔仁大學 === 化學系 === 106 === Starting from D-ribose, the C(2) and C(3) hydroxyl group was protected, then carry out Witting reaction to get chain compound. Selective bromination of the hydroxyl group, protection, and ozone cleavage reaction to obtain an aldehyde radical precursor. The key of radical reaction was achieved within only 7 min by direct addition a mixed solution of AIBN and Bu3SnH in toluene. In addition, also tried to replace Bu3SnH with TTMSS. But, the yield of radical products is poor. Then, the radical product of aldehyde group was protected by dithioacetal. After several steps to deprotected, 2-deoxy-L-ribose derivatives was obtained. In addition, The obtained X-ray crystal structure confirmed the stereochemistry of the corresponding radical product. However, if the radical product of aldehyde group was protected by ethanethiol. After several steps of functional group protection and cyclization, a good glycosyl donor of 2-deoxy-L-ribose can be obtained, and then the glycosylation reaction with the nitrogen-containing base can be obtained to 2-deoxy-L-nucleosides
Keywords: D-ribose、2-deoxy-L-ribose、2-deoxy-L-nucleosides
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