5 ' -脱氧-5-氟吡啶与1-?- d -阿拉伯糖脲基胞嘧啶与二磷酸二钠

Phosphorus Research Bulletin Pub Date : 2020-01-01 DOI:10.3363/prb.36.29

Hideko Maeda, Tadashi Matsushima, Takeshi Nagai, H. Nakayama

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引用次数: 0

摘要

用二磷酸二钠(DP, Na2P2O5H2)在水溶液中成功地进行了5 ' -脱氧-5-氟吡啶(5 ' - dfur)和1-- d -阿拉伯糖醛酸胞嘧啶(Ara C)的磷酸化。前一反应合成了3′-膦基-5′-DFUR和2′-膦基-5′-DFUR，总收率为100%。1-- d -阿拉伯糖醛酸胞嘧啶(Ara C)与DP反应得到5′-膦基Ara C、3′-膦基Ara C和2′-膦基Ara C，总收率大于35%。5′-DFUR或Ara C与DP磷酸化的最佳条件为5′-DFUR或Ara C与DP的比例为1:10，溶液pH为11。在7 ~ 9的pH范围内，5′-DFUR和Ara C的磷酸化产物分别在10℃和25℃下稳定。提出了5′-DFUR和Ara C与DP反应的机理。(2020年11月10日收稿;2020年11月30日录用)

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PHOSPHONYLATION OF 5’-DEOXY-5-FLUOROURIDINE AND 1-?-D-ARABINOFURANOSYLCYTOSINE WITH DISODIUM DIPHOSPHONATE

Phosphonylations of 5’-deoxy-5-fluorouridine (5’-DFUR) and 1--D-arabinofuranosylcytosine (Ara C) in aqueous solution were successfully performed using disodium diphosphonate (DP, Na2P2O5H2). The former reaction resulted in the synthesis of both 3’-phosphonyl-5’-DFUR and 2’-phosphonyl-5’-DFUR, with an overall yield of 100%. The reaction of 1--D-arabinofuranosylcytosine (Ara C) with DP gave 5’-phosphonyl-Ara C, 3’-phosphonyl-Ara C and 2’-phosphonyl-Ara C in a total yield of more than 35%. The optimal condition for the phosphonylation of either 5’-DFUR or Ara C with DP was determined to be a 1:10 ratio of 5’-DFUR or Ara C to DP and a solution pH of 11. The phosphonylated products of 5’-DFUR and Ara C were stable at 10 oC and 25 oC, respectively, over the pH range of 7 to 9. A proposed mechanism for the reactions of 5’-DFUR and Ara C with DP was developed. (Received Nov 10, 2020; Accepted Nov 30, 2020)

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Phosphorus Research Bulletin

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