A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides
A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides
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DOI：
10.1016/s0040-4020(02)00230-2
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发表时间：
2002-04-15
期刊：
影响因子：
2.1
通讯作者：
Wu, YL
中科院分区：
文献类型：
--
作者：
Shi, ZD;Yang, BH;Wu, YL
以手性池中廉价的D-半乳糖为原料，在温和的反应条件下合成了L-脱氧核糖、L-核糖及其衍生物。在L-脱氧核糖的合成过程中，3，5-O-二苄基-甲基-L-阿拉伯呋喃糖苷的2-羟基的关键脱氧是用四丁基硼氢化铵还原相应的三氟甲磺酸酯，产率较高。在L-核糖的合成过程中，同一底物上的2-羟基的转化这一关键步骤是通过分子内S（N）2串联反应完成的。然后将L-核糖基供体按照Vorbruggen的条件进行糖苷化，以优异的产率得到L-核苷（L-尿苷、L-5-氟尿苷、L-碘尿苷、L-胸苷、L-嘌呤苷、L-腺苷和L-鸟苷）。(C)2002爱思唯尔科技有限公司。保留所有权利。
Using an inexpensive D-galactose from the chiral Pool, L-deoxyribose, L-ribose and their derivatives were synthesized via mild reaction conditions. During the synthesis Of L-deoxyribose, the key deoxygenation of the 2-hydroxy group of 3,5-O-dibenzyl-methyl-L-arabinofuranoside was performed by reduction of the corresponding triflate with tetrabutylammonium borohydride in high yield. During the synthesis Of L-ribose, the key step of inversion of the 2-hydroxy group in the same substrate was carried out by intramolecular S(N)2 tandem reaction. Then the L-ribosyl donors were submitted to glycosidations according to Vorbruggen's conditions to give L-ribosides (L-uridine, L-5-fluorouridine, L-iodouridine, L-thymidine, L-puridine, L-adenosine and L-guanosine) in excellent yields. (C) 2002 Elsevier Science Ltd. All rights reserved.