3',5'-di-O-acetyl-2'-deoxy-4'-C-methyluridine | 175545-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3',5'-di-O-acetyl-2'-deoxy-4'-C-methyluridine
• 英文别名: [(2R,3S,5R)-3-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-methyloxolan-2-yl]methyl acetate
• CAS: 175545-22-9
• 化学式: C₁₄H₁₈N₂O₇
• 分子量: 326.306
• InChiKey: PBPWZDQYBPOTTI-ZKYQVNSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-acetyl-2'-deoxy-4'-C-methyluridine 在 palladium diacetate 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 ammonium cerium(IV) nitrate 、 碘 、 potassium hydrogencarbonate 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 5-((E)-2-Bromo-vinyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-methyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of novel 4′-C-methyl-pyrimidine nucleosides and their biological activities

  摘要：

  Two novel 4'-C-methylnucleosides, 4'-methylBVDU 9 and 4'-methylBVaraU 10, were synthesized. The farmer was derived from 3',5'-di-O-acetyl-2'-deoxy-4'-C-methyluridine 12, and the latter was produced via glycosylation between 4-C-methyl-D-ribose derivative 11 and a silylated bromovinyl uracil. 4'-MethylBVDU 9 exhibited particularly potent anti-varicella-zoster virus (VZV) activity in vitro. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00090-6
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-4-bromo-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-methyl-tetrahydro-furan-3-yl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 、 苯 为溶剂， 以22%的产率得到2,2'-anhydro-3',5'-di-O-acetyl-2'-deoxy-4'-C-methyluridine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 4′-C-Methyl Nucleosides

  摘要：

  A series of 2'-deoxy, 2',3'-unsaturated and 2',3'-dideoxynucleoside analogues, which have an additional methyl group at the 4'-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2'-deoxy-4'-C-methyl nucleosides exhibited potent activity.

  DOI：

  10.1080/07328319608002385

文献信息

• Synthesis of 4′-C-alkylated-5-iodo-2′-deoxypyrimidine nucleosides
  作者：Tobias Strittmatter、Joos Aschenbrenner、Norman Hardt、Andreas Marx

  DOI：10.3998/ark.5550190.0014.206

  日期：——

  Starting from available ribose-building blocks, the 4 '-C-methyl-, 4 '-C-ethyl- and the new 4 '-C- propyl-substituted deoxyuridines were synthesized. Afterwards we converted 4 '-C-alkylated-2'- deoxyuridines into the corresponding 4 '-C-alkylated-5-iodo-2'-deoxyuridines 3a-c and those in turn into the 4 '-C-alkylated-5-iodo-2'-deoxycytidines 4a-c.

  从可用的核糖结构单元开始，合成了 4'-C-甲基-、4'-C-乙基-和新的 4'-C-丙基-取代的脱氧尿苷。之后，我们将 4'-C-烷基化-2'-脱氧尿苷转化为相应的 4'-C-烷基化-5-碘-2'-脱氧尿苷 3a-c，然后将它们转化为 4'-C-烷基化-5-碘-2'-脱氧胞苷 4a-c。