Synthesis of branched ribofuranans and their sulfates with strong anti-AIDS virus activity by selective ring-opening copolymerization of 1,4-anhydro-α-D-ribopyranose derivatives.
Synthesis of branched ribofuranans and their sulfates with strong anti-AIDS virus activity by selective ring-opening copolymerization of 1,4-anhydro-α-D-ribopyranose derivatives.
复制标题
通过1,4-脱水-α-D-吡喃核糖衍生物的选择性开环共聚合成具有强抗艾滋病病毒活性的支链呋喃核糖及其硫酸盐。
DOI：
10.1021/ma00042a001
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发表时间：
1992
期刊：
影响因子：
5.5
通讯作者：
T. Uryu
中科院分区：
文献类型：
--
作者：
Takashi Yoshida;Y. Katayama;S. Inoue;T. Uryu
以三氟化硼醚为催化剂，以不同比例的1,4-无氢-2,3-二-0-苄基-和1,4-无氢-2,3-二-o -（叔丁基二甲基硅基）-α- d -核吡喃为原料，在ch2cl 2中选择性开环共聚合成了立体规则（1→5）-α- d -核呋喃（α-D-R）衍生物。选择性去除硅基得到由1,5-α- d -核呋喃烷基和苯基化的1,5-α- d -核呋喃烷基组成的α-D-R。与D-甘露糖、D-葡萄糖和l -葡萄糖正构酯反应后脱保护，得到具有2位和/或3位分支的α-D-R
Stereoregular (1→5)-α-D-ribofuranan (α-D-R) derivatives were synthesized by selective ring-opening copolymerization in the various ratio of 1,4-anhydro-2,3-di-0-benzyl- and 1,4-anhydro-2,3-di-O-(tert-butyldimethylsilyl)- α-D-ribopyranoses with boron trifluoride etherate as catalyst in CH 2 Cl 2 . Selective removal of the silyl groups gave α-D-R which are composed of 1,5-α-D-ribofuranosidic units and benzylated 1,5-α-D-ribofuranosidic units. Branched α-D-R having branches at 2- and/or 3-positions were obtained after reaction with D-mannose, D- and L-glucose orthoesters followed by deprotection