Minamoto K, Watanabe K, Yanagihara K
Department of Applied Chemistry, School of Engineering, Nagoya University, Japan.
Nucleic Acids Symp Ser. 1992(27):109-10.
The reaction of 1-(2,3-anhydro-5-O-trityl-beta-D-lyxofuranosyl)-2-O-methyluracil (1a) and its thymine analogue (1b) with dilithium tetrahalocuprate (Li2CuX4) revealed excellent to perfect regioselectivity, yielding 2,2'-anhydro-3'-halonucleosides (2a-d), while the same reactions with 2,3-anhydro uracil and thymine nucleosides (4a,b) gave arabinosyl (5a-d) and xylosyl halohydrins (6a-d) with the respective product ratio of 7:3 to 8:2. compounds 5 and 6 were isolated as the 2-O-(7) and 3- O-mesyl derivatives (8).
1-(2,3-脱水-5-O-三苯甲基-β-D-呋喃来苏糖基)-2-O-甲基尿嘧啶(1a)及其胸腺嘧啶类似物(1b)与四卤化铜酸二锂(Li2CuX4)反应显示出优异至完美的区域选择性，生成2,2'-脱水-3'-卤代核苷(2a-d)，而2,3-脱水尿嘧啶和胸腺嘧啶核苷(4a,b)的相同反应则生成阿拉伯糖基(5a-d)和木糖基卤代醇(6a-d)，各自的产物比例为7:3至8:2。化合物5和6分别作为2-O-(7)和3-O-甲磺酰基衍生物(8)被分离出来。
