Carbonic acid allyl ester (2S,3S,4S,6R)-4-allyloxycarbonylamino-6-[(1S,3S)-3-(2-bromo-2-fluoro-acetyl)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester | 444910-66-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: Carbonic acid allyl ester (2S,3S,4S,6R)-4-allyloxycarbonylamino-6-[(1S,3S)-3-(2-bromo-2-fluoro-acetyl)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2S,3S,4S,6R)-6-[[(1S,3S)-3-(2-bromo-2-fluoroacetyl)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-2-methyl-4-(prop-2-enoxycarbonylamino)oxan-3-yl] prop-2-enyl carbonate
• CAS: 444910-66-1
• 化学式: C₃₅H₃₅BrFNO₁₄
• 分子量: 792.564
• InChiKey: BTEICUDSVHZKCF-GSMWVVFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  213
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Carbonic acid allyl ester (2S,3S,4S,6R)-4-allyloxycarbonylamino-6-[(1S,3S)-3-(2-bromo-2-fluoro-acetyl)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester 在 四(三苯基膦)钯 silver tetrafluoroborate 、 N,N-二甲基三甲基硅胺 、 三甲基硅乙酸酯 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (8S,10S)-10-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-8-(2-fluoro-2-hydroxy-acetyl)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione
  参考文献：
  名称：

  Synthesis of 14-fluorodoxorubicin

  摘要：

  Abstraet-Synthesis of the novel anthracycline 14-fluorodoxorubicin is described. A key step in the synthesis is the hydrolysis of 14-bromo,14-fluoro derivative 14 with AgBF4 and DMSO, to give the geminal fluorohydrin system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00299-x
• 作为产物：
  描述：

  1-O-p-nitrobenzoyl-3-N,4-O-di-allyloxycarbonyl-L-daunosamine 、 (8S,10S)-8-(2-Bromo-2-fluoro-acetyl)-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以54%的产率得到Carbonic acid allyl ester (2S,3S,4S,6R)-4-allyloxycarbonylamino-6-[(1S,3S)-3-(2-bromo-2-fluoro-acetyl)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of 14-fluorodoxorubicin

  摘要：

  Abstraet-Synthesis of the novel anthracycline 14-fluorodoxorubicin is described. A key step in the synthesis is the hydrolysis of 14-bromo,14-fluoro derivative 14 with AgBF4 and DMSO, to give the geminal fluorohydrin system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00299-x

文献信息

• Synthesis of 14-fluorodoxorubicin
  作者：M. Berettoni、A. Cipollone、L. Olivieri、D. Palomba、F. Arcamone、C.A. Maggi、F. Animati

  DOI：10.1016/s0040-4039(02)00299-x

  日期：2002.4

  Abstraet-Synthesis of the novel anthracycline 14-fluorodoxorubicin is described. A key step in the synthesis is the hydrolysis of 14-bromo,14-fluoro derivative 14 with AgBF4 and DMSO, to give the geminal fluorohydrin system. (C) 2002 Elsevier Science Ltd. All rights reserved.