LITHIATION OF 5,6-DIHYDROURIDINE - A NEW ROUTE TO 5-SUBSTITUTED URIDINES
LITHIATION OF 5,6-DIHYDROURIDINE - A NEW ROUTE TO 5-SUBSTITUTED URIDINES
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DOI：
10.1016/s0040-4020(01)96481-6
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发表时间：
1985-01-01
期刊：
影响因子：
2.1
通讯作者：
MIYASAKA, T
中科院分区：
文献类型：
--
作者：
HAYAKAWA, H;TANAKA, H;MIYASAKA, T
发现2“，3”-O-异亚丙基-5“-O-甲氧基甲基-5，6-二氢尿苷（2）作为“酰胺α-阴离子”。该阴离子与酰氯反应，然后进行苯硒化和氧化消除，得到5-酰基尿苷。对于5-烷基尿苷的制备，在2的C-5处初始引入苯基硒基似乎是有效的。其α-烷基化硒基碳负离子和随后产生的5，6-双键产生5-烷基尿苷。这些路线构成了5-取代尿苷的新条目。
2'',3''-O-Isopropylidene-5''-O-methoxymethyl-5,6-dihydrouridine (2) was found to serve as an "amide .alpha.-anion" upon lithiation with LDA. Reactions of the anion with acid chlorides followed by phenylselenation and oxidative elimination furnished 5-acyluridines. For the preparation of 5-alkyluridines, initial introduction of phenylselenenyl group at the C-5 of 2 appeared to be effective. Alkylation of its .alpha.-selenenyl carbanion and subsequent generation of 5,6-double bond produced 5-alkyluridines. These routes constitute a new entry to 5-substituted uridines.