1-((3S,4R,5R)-5-Dimethoxymethyl-4-hydroxy-tetrahydro-furan-3-yl)-5-methyl-1H-pyrimidine-2,4-dione | 174860-95-8

• 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: 1-((3S,4R,5R)-5-Dimethoxymethyl-4-hydroxy-tetrahydro-furan-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 174860-95-8
• 化学式: C₁₂H₁₈N₂O₆
• 分子量: 286.285
• InChiKey: YUJIKQBJJUORBG-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.24
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  102.78
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-((3S,4R,5R)-5-Dimethoxymethyl-4-hydroxy-tetrahydro-furan-3-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 反应 3.67h， 生成 1,4-anhydro-2-deoxy-2-(thymin-1-yl)-L-arabinitol
  参考文献：
  名称：

  Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines

  摘要：

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00048-x
• 作为产物：
  描述：

  2,5-Anhydro-D-xylose dimethyl acetal 3-(4-methylbenzenesulfonate) 在 18-冠醚-6 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 79.0h， 生成 1-((3S,4R,5R)-5-Dimethoxymethyl-4-hydroxy-tetrahydro-furan-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines

  摘要：

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00048-x

文献信息

• Synthesis of 2S-(2-hydroxyethyl)-3R-hydroxy-4S-(thymin-1-yl or adenin-9-yl)-tetrahydrofuran
  作者：Ying-Chun Liu、Jun Zhang、Lei Xing、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.tet.2008.07.039

  日期：2008.9

  strategies were developed to obtain isonucleosides 2a and 2b. Starting from the known compound 4, an extension of one carbon unit at sugar 6-terminal was achieved by Wittig reaction and Stannyl-desulfonylation reaction. After oxidation of the double bond, the isonucleosides with elongated side chain 2a and 2b were synthesized. For the synthesis of isonucleosides containing different bases, an epoxide

  开发了两种合成策略以获得异核苷2a和2b。从已知化合物4开始，通过Wittig反应和Stannyl-脱磺酰化反应实现了糖6-末端一个碳单元的延伸。双键氧化后，合成了具有延长的侧链2a和2b的异核苷。为了合成含有不同碱基的异核苷，开发了一种环氧化物中间体方法。通过18的区域选择性环氧化物开环反应以高收率合成了异核苷2a和2b。