tert-butyl (3aS,4R,5S,7S,7aR)-4-acetamido-7-((tert-butyldimethylsilyloxy)dicyanomethyl)-2,2-dimethyl-hexahydrobenzo[d][1,3]dioxol-5-ylcarbamate | 1184177-26-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (3aS,4R,5S,7S,7aR)-4-acetamido-7-((tert-butyldimethylsilyloxy)dicyanomethyl)-2,2-dimethyl-hexahydrobenzo[d][1,3]dioxol-5-ylcarbamate
• 英文别名: tert-butyl N-[(3aS,4R,5S,7S,7aR)-4-acetamido-7-[[tert-butyl(dimethyl)silyl]oxy-dicyanomethyl]-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl]carbamate
• CAS: 1184177-26-1
• 化学式: C₂₅H₄₂N₄O₆Si
• 分子量: 522.717
• InChiKey: QYKTUCCLKPBDCO-OMZCGLGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (3aS,4R,5S,7S,7aR)-4-acetamido-7-((tert-butyldimethylsilyloxy)dicyanomethyl)-2,2-dimethyl-hexahydrobenzo[d][1,3]dioxol-5-ylcarbamate 在 乙醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 triethylamine tris(hydrogen fluoride) 作用下， 反应 36.0h， 以76%的产率得到ethyl (3R,4R,5S)-4-acetamido-5-(tert-butoxycarbonylamino)-3-hydroxycyclohex-1-enecarboxylate
  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：

  在 ruthenium trichloride 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,1'-双(二苯基膦)二茂铁 、 sodium periodate 、 硫酸 、 水 、 对甲苯磺酸 作用下， 以 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 2.83h， 生成 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

文献信息

• An alternative synthesis of Tamiflu®: a synthetic challenge and the identification of a ruthenium-catalyzed dihydroxylation route
  作者：Kenzo Yamatsugu、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1016/j.tet.2009.05.077

  日期：2009.8

  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,