5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(oxo-1-ethane)-thymidine | 224157-46-4

• 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: 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(oxo-1-ethane)-thymidine
• 英文别名: (3S)-3-[(2S,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-3-trimethylsilyloxypropanal
• CAS: 224157-46-4
• 化学式: C₃₁H₄₂N₂O₆Si₂
• 分子量: 594.855
• InChiKey: LURYAYAATQBBKN-YVHASNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(oxo-1-ethane)-thymidine 在 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 6.08h， 生成 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(hex-4-ene-1-ol)-thymidine
  参考文献：
  名称：

  Allylsilanes in the preparation of 5′-C-hydroxy or bromo alkylthymidines

  摘要：

  The reaction of 5'-C-thymidine aldehyde with allytrimethylsilane promoted by BF3:Et2O lead stereoselectively to 5'-C(S)-allylthymidine which is converted to 5'-C(S) C(S)-hydroxyhexylthymidine. 5'-C-(R or S) hydroxypentylthymidine can be obtained by using omega-tertButyldimethylsilyloxyallyltrimethylsilane in the Sakurai reaction. In the same conditions, omega-Bromoallyltrimethylsilane adds to the aldehyde with a complete transposition of the siliranium intermediate and allows the preparation of the 5'-C(S)-bromopentene derivative, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00246-x
• 作为产物：
  描述：

  (S)-3-[(2S,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-3-trimethylsilanyloxy-propionic acid methyl ester 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以95%的产率得到5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(oxo-1-ethane)-thymidine
  参考文献：
  名称：

  Allylsilanes in the preparation of 5′-C-hydroxy or bromo alkylthymidines

  摘要：

  The reaction of 5'-C-thymidine aldehyde with allytrimethylsilane promoted by BF3:Et2O lead stereoselectively to 5'-C(S)-allylthymidine which is converted to 5'-C(S) C(S)-hydroxyhexylthymidine. 5'-C-(R or S) hydroxypentylthymidine can be obtained by using omega-tertButyldimethylsilyloxyallyltrimethylsilane in the Sakurai reaction. In the same conditions, omega-Bromoallyltrimethylsilane adds to the aldehyde with a complete transposition of the siliranium intermediate and allows the preparation of the 5'-C(S)-bromopentene derivative, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00246-x

文献信息

• Allylsilanes in the preparation of 5′-C-hydroxy or bromo alkylthymidines
  作者：Valérie Banuls、Jean-Marc Escudier

  DOI：10.1016/s0040-4020(99)00246-x

  日期：1999.4

  The reaction of 5'-C-thymidine aldehyde with allytrimethylsilane promoted by BF3:Et2O lead stereoselectively to 5'-C(S)-allylthymidine which is converted to 5'-C(S) C(S)-hydroxyhexylthymidine. 5'-C-(R or S) hydroxypentylthymidine can be obtained by using omega-tertButyldimethylsilyloxyallyltrimethylsilane in the Sakurai reaction. In the same conditions, omega-Bromoallyltrimethylsilane adds to the aldehyde with a complete transposition of the siliranium intermediate and allows the preparation of the 5'-C(S)-bromopentene derivative, (C) 1999 Elsevier Science Ltd. All rights reserved.