Carbon-Carbon Bond Formation at the Sugar Portion of Nucleosides : Synthetic Potential of Unsaturated-sugar Nucleosides
Carbon-Carbon Bond Formation at the Sugar Portion of Nucleosides : Synthetic Potential of Unsaturated-sugar Nucleosides
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核苷糖部分碳-碳键的形成：不饱和糖核苷的合成潜力
DOI：
10.5059/yukigoseikyokaishi.61.974
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发表时间：
2003
影响因子：
0.2
通讯作者：
Hiromichi Tanaka
中科院分区：
文献类型：
--
作者：
K. Haraguchi;Y. Itoh;Hiromichi Tanaka
不饱和糖核苷已被证明是在糖部分构建C-C键的通用底物。对1 ′，2 ′-，2 ′，3 ′-，3 ′，4 ′-和4 ′，5 ′-不饱和衍生物采用各种类型的适当反应。这些反应包括亲电加成反应、有机硅和有机铝试剂取代反应、自由基介导的加成物的1，2-酰氧基迁移反应、苯硫酚亲核加成反应、自由基取代反应、烯醇酯的羟醛缩合反应、Pd催化的核苷溴代乙烯基的交叉偶联反应和卤素-锂交换反应、SN 2 '反应、碳自由基加成反应、和用有机金属试剂进行环氧开环。因此，在核苷的1 ′-、2 ′-、3 ′-、4 ′-和5 ′-位上形成C-C键成为可能。
Unsaturated-sugar nucleosides have been shown to serve as versatile substrates for constructing C-C bond at the sugar portion. Various types of appropriate reactions were adopted to 1', 2'-, 2', 3'-, 3', 4'-, and 4', 5'-unsaturated derivatives. These are electrophilic addition followed by substitution with organosilicon and organoaluminum reagents, radical-mediated 1, 2-acyloxy migration of the adducts, nucleophilic addition of benzenethiolate followed by radical substitution, aldol reaction of an enol ester, Pd-catalyzed cross-coupling and halogen-lithium exchange reactions of nucleosidic vinyl bromides, SN2' reaction, addition reaction of carbon radicals, and epoxide ring opening with organometallic reagents. Consequently, C-C bond formation at the 1'-, 2'-, 3'-, 4'-, and 5'-positions of nucleoside became possible.