Synthesis of 2',3'-Dideoxy-3'-C-(hydroxymethyl)-4'-thionucleosides as Potential Inhibitors of HIV
Synthesis of 2',3'-Dideoxy-3'-C-(hydroxymethyl)-4'-thionucleosides as Potential Inhibitors of HIV
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2,3-二脱氧-3-C-(羟甲基)-4-硫代核苷作为 HIV 潜在抑制剂的合成
DOI：
10.1021/jo00086a032
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发表时间：
1994
期刊：
影响因子：
--
通讯作者：
B. Samuelsson
中科院分区：
文献类型：
--
作者：
J. Braanalt;I. Kvarnstroem;G. Niklasson;S. Svensson;Bjoern Classon;B. Samuelsson
本文报道了2 ′，3 ′-双脱氧-3 ′-C-（氢甲基）-4 ′-硫代糖苷的合成。对于碳水化合物部分的合成，使用Mitsunobu反应条件反转（2S，3R）-1-O-（对溴苄基）-3-（2 '-丙烯基）-1，2，4-丁三醇（1）中仲羟基的构型，然后使用相转移催化对产物2中的伯羟基进行区域选择性苯甲酰基化。烯丙基双键的氧化断裂，然后关环和对溴苄基保护基的交换得到甲基呋喃糖苷衍生物5，其进一步转化为相应的二苄基二硫缩醛6
The synthesis of 2',3'-dideoxy-3'-C-(hydrorymethyl)-4'-thionucleosides is described. For the synthesis of the carbohydrate part, the configuration of the secondary hydroxyl group in (2S,3R)-1-O-(p-bromobenzyl)-3-(2'-propenyl)-1,2,4-butanetriol (1) was inverted using Mitsunobu reaction conditions, after which the primary hydroxyl group in product 2 was regioselectively benzoylated using phase-traasfer catalysis. Oxidative cleavage of the allylic double bond, followed by ring closure and exchange of the p-bromobenzyl protecting group gave the methyl furanoside derivative 5, which was further converted to the corresponding dibenzyl dithioacetal 6