acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester | 234755-06-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester
• 英文别名: tert-butyl (1S,4R)-2-[N-(9H-fluoren-9-ylmethoxycarbonyl)-benzylamino]-(1-acetoxymethyl-4-trimethylsilylbut-3-ynyl)carbamate；[(2R,3S)-3-[benzyl(9H-fluoren-9-ylmethoxycarbonyl)amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-trimethylsilylpent-4-ynyl] acetate
• CAS: 234755-06-7
• 化学式: C₃₇H₄₄N₂O₆Si
• 分子量: 640.852
• InChiKey: ZHWDLTHVOWQLDT-HEVIKAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester 在 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以95%的产率得到acetic acid 3(S)-{benzyl-[(9H-fluoren-9-yl-methoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}pent-4-yn-1-yl ester
  参考文献：
  名称：

  Use of Catalytic Fluoride under Neutral Conditions for Cleaving Silicon–Oxygen Bonds

  摘要：

  This Article describes the development of conditions for cleaving silicon oxygen bonds using catalytic quantities of fluoride at neutral pH in mixed organic aqueous solutions that contain buffer. A variety of silicon protecting groups can be removed under these conditions, which show tolerance for acid- and base-sensitive groups. A modified procedure also is presented using catalytic fluoride in anhydrous dimethyl sulfoxide-methanol, which generates primarily volatile silicon byproducts.

  DOI：

  10.1021/jo200848j
• 作为产物：
  描述：

  (R)-4-[(E)-Benzylimino-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 正丁基锂 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 36.5h， 生成 acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester
  参考文献：
  名称：

  Alkylidenecarbene Insertion into a Nitrogen Lone Pair: An Unexpected Synthesis of Dihydropyrroles from Alkynyliodonium Salts

  摘要：

  DOI：

  10.3987/com-99-8481

文献信息

• Use of Catalytic Fluoride under Neutral Conditions for Cleaving Silicon–Oxygen Bonds
  作者：Anthony M. DiLauro、Wanji Seo、Scott T. Phillips

  DOI：10.1021/jo200848j

  日期：2011.9.16

  This Article describes the development of conditions for cleaving silicon oxygen bonds using catalytic quantities of fluoride at neutral pH in mixed organic aqueous solutions that contain buffer. A variety of silicon protecting groups can be removed under these conditions, which show tolerance for acid- and base-sensitive groups. A modified procedure also is presented using catalytic fluoride in anhydrous dimethyl sulfoxide-methanol, which generates primarily volatile silicon byproducts.
• Alkylidenecarbene Insertion into a Nitrogen Lone Pair: An Unexpected Synthesis of Dihydropyrroles from Alkynyliodonium Salts
  作者：Ken S. Feldman、Pamela A. Mingo、Paul C. D. Hawkins

  DOI：10.3987/com-99-8481

  日期：——