Benzoic acid (2R,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,3-difluoro-tetrahydro-thiophen-2-ylmethyl ester | 799257-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (2R,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,3-difluoro-tetrahydro-thiophen-2-ylmethyl ester
• 英文别名: [(2R,4R)-4-(2,4-dioxopyrimidin-1-yl)-3,3-difluorothiolan-2-yl]methyl benzoate
• CAS: 799257-38-8
• 化学式: C₁₆H₁₄F₂N₂O₄S
• 分子量: 368.361
• InChiKey: ZOWFWHBAPJPFNJ-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,3-difluoro-tetrahydro-thiophen-2-ylmethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 以70 mg的产率得到1-(4,4-difluoro-5-hydroxymethyltetrahydrothiophen-3-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of New 2‘,3‘-Dideoxy-6‘,6‘-difluoro-3‘-thionucleoside from gem-Difluorohomoallyl Alcohol

  摘要：

  [GRAPHICS]2',3'-Dideoxy-6',6'-difluoro-3'-thionucleoside 1b, an analogue of 3Tc that has high biological activities against HIV and HBV, has been synthesized from gem-difluorohomoallyl alcohol 3 in an efficient way. The key intermediate 4-amino-3,3-difluorotetrahydrothiophen-2-ylmethyl benzoate 15 was prepared from 2,2-difluoro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol 3 in 11 steps. The construction of pyrimidine ring with the amino group of compound 15 gave the target compound 1.

  DOI：

  10.1021/ol048423j
• 作为产物：
  描述：

  benzoic acid 4-[3-(3ethoxyacryloyl)ureido]-3,3-difluorotetrahydrothiophen-2-ylmethyl ester 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 Benzoic acid (2R,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,3-difluoro-tetrahydro-thiophen-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis of New 2‘,3‘-Dideoxy-6‘,6‘-difluoro-3‘-thionucleoside from gem-Difluorohomoallyl Alcohol

  摘要：

  [GRAPHICS]2',3'-Dideoxy-6',6'-difluoro-3'-thionucleoside 1b, an analogue of 3Tc that has high biological activities against HIV and HBV, has been synthesized from gem-difluorohomoallyl alcohol 3 in an efficient way. The key intermediate 4-amino-3,3-difluorotetrahydrothiophen-2-ylmethyl benzoate 15 was prepared from 2,2-difluoro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol 3 in 11 steps. The construction of pyrimidine ring with the amino group of compound 15 gave the target compound 1.

  DOI：

  10.1021/ol048423j

文献信息

• Synthesis of New 2‘,3‘-Dideoxy-6‘,6‘-difluoro-3‘-thionucleoside from <i>g</i><i>em</i>-Difluorohomoallyl Alcohol
  作者：Yun-Yun Wu、Xingang Zhang、Wei-Dong Meng、Feng-Ling Qing

  DOI：10.1021/ol048423j

  日期：2004.10.1

  [GRAPHICS]2',3'-Dideoxy-6',6'-difluoro-3'-thionucleoside 1b, an analogue of 3Tc that has high biological activities against HIV and HBV, has been synthesized from gem-difluorohomoallyl alcohol 3 in an efficient way. The key intermediate 4-amino-3,3-difluorotetrahydrothiophen-2-ylmethyl benzoate 15 was prepared from 2,2-difluoro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol 3 in 11 steps. The construction of pyrimidine ring with the amino group of compound 15 gave the target compound 1.