tert-butyl (1S,2R,3S,4R,5S)-2-acetamido-5-((tert-butyldimethylsilyloxy)dicyanomethyl)-3,4-dihydroxycyclohexylcarbamate | 1184177-25-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl (1S,2R,3S,4R,5S)-2-acetamido-5-((tert-butyldimethylsilyloxy)dicyanomethyl)-3,4-dihydroxycyclohexylcarbamate
• 英文别名: tert-butyl N-[(1S,2R,3S,4R,5S)-2-acetamido-5-[[tert-butyl(dimethyl)silyl]oxy-dicyanomethyl]-3,4-dihydroxycyclohexyl]carbamate
• CAS: 1184177-25-0
• 化学式: C₂₂H₃₈N₄O₆Si
• 分子量: 482.652
• InChiKey: SJXZMSJLEAGQCN-AVEIZBFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2R,3S,4R,5S)-2-acetamido-5-((tert-butyldimethylsilyloxy)dicyanomethyl)-3,4-dihydroxycyclohexylcarbamate 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以32.8 mg的产率得到tert-butyl (3aS,4R,5S,7S,7aR)-4-acetamido-7-((tert-butyldimethylsilyloxy)dicyanomethyl)-2,2-dimethyl-hexahydrobenzo[d][1,3]dioxol-5-ylcarbamate
  参考文献：
  名称：

  An alternative synthesis of Tamiflu®: a synthetic challenge and the identification of a ruthenium-catalyzed dihydroxylation route

  摘要：

  Synthetic studies of Tamiflu (R) and the identification of a ruthenium-catalyzed dihydroxylation route are disclosed. This newly developed synthetic process circumvents the need for a Mitsunobu inversion step and the use of explosive reagents. This route, therefore, compares favorably to the previously developed synthetic process. (C) 2009 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2009.05.077
• 作为产物：
  描述：

  tert-butyl (1S,2S,5S)-2-acetamido-5-((tert-butyldimethylsilyloxy)dicyanomethyl)cyclohex-3-enylcarbamate 在 ruthenium trichloride 、 sodium periodate 、 硫酸 、 水 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 1.33h， 生成 tert-butyl (1S,2R,3S,4R,5S)-2-acetamido-5-((tert-butyldimethylsilyloxy)dicyanomethyl)-3,4-dihydroxycyclohexylcarbamate
  参考文献：
  名称：

  An alternative synthesis of Tamiflu®: a synthetic challenge and the identification of a ruthenium-catalyzed dihydroxylation route

  摘要：

  Synthetic studies of Tamiflu (R) and the identification of a ruthenium-catalyzed dihydroxylation route are disclosed. This newly developed synthetic process circumvents the need for a Mitsunobu inversion step and the use of explosive reagents. This route, therefore, compares favorably to the previously developed synthetic process. (C) 2009 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2009.05.077