tert-butyl N-<9-allyl-13-<(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl>-16-(trifluoroacetamido)-4-<2-(trimethylsilyl)ethylsulfonyl>-4,9,13-triazahexadecyl>carbamate | 220095-04-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: tert-butyl N-<9-allyl-13-<(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl>-16-(trifluoroacetamido)-4-<2-(trimethylsilyl)ethylsulfonyl>-4,9,13-triazahexadecyl>carbamate
• 英文别名: (1,1,1-trichloro-2-methylpropan-2-yl) N-[3-[4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl-(2-trimethylsilylethylsulfonyl)amino]butyl-prop-2-enylamino]propyl]-N-[3-[(2,2,2-trifluoroacetyl)amino]propyl]carbamate
• CAS: 220095-04-5
• 化学式: C₃₃H₆₁Cl₃F₃N₅O₇SSi
• 分子量: 863.382
• InChiKey: WUIJBYVSPBVKEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  53.0
• 可旋转键数：
  24.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  137.59
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-<9-allyl-13-<(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl>-16-(trifluoroacetamido)-4-<2-(trimethylsilyl)ethylsulfonyl>-4,9,13-triazahexadecyl>carbamate 在 锌 作用下， 以 溶剂黄146 为溶剂， 反应 20.0h， 以70%的产率得到tert-butyl N-<9-allyl-16-(trifluoroacetamido)-4-<2-(trimethylsilyl)ethylsulfonyl>-4,9,13-triazahexadecyl>carbamate
  参考文献：
  名称：

  Regioselective Deprotection and Acylation of Penta-N-Protected Thermopentamine

  摘要：

  The synthesis of the penta-N-protected polyamide 1 (ten-butyl N-{9-allyl-16-azido-13-(trinuoroacetyl)-4-[2-(trimethylsilyl)ethylsulfonyl]-4,9,13-triazahexadecyl]carbamate = tert-butyl N-{3-{[4-{allyl[3-[(3-azidopropyl)(trifluoroacetyl)aminopropyl}amino}butyl}{[2-(trimethylsilyl)ethyl]sulfonyl}amino}propyl}carbamate) is described, a derivative of thermopentamine (PA 3433) containing five independently removable amino-protecting groups. The selective deprotection of the five protecting groups used, it., of allyl, azido, (tert-butoxy)carbonyl (Boc). trifluoroacetyl, and [2-(trimethylsilyl)ethyl]sulfonyl (SES), as well as the rapid transamidation reaction of the trifluoroacetyl group yielding secondary amides is discussed. Subsequent acylation with 4-methoxycinnamoyl chloride at each N-atom of the pentamine backbone is achieved. For the acylation of the terminal N-atom the azido group is replaced by a (2,2,2-trichloro-1,l-dimethylethoxy)carbonyl (Tcboc) group.

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2300::aid-hlca2300>3.0.co;2-7
• 作为产物：
  描述：

  N-(3-azidopropyl)-3-aminopropan-1-ol 在 4-二甲氨基吡啶 、 水 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 sodium hydroxide 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 190.0h， 生成 tert-butyl N-<9-allyl-13-<(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl>-16-(trifluoroacetamido)-4-<2-(trimethylsilyl)ethylsulfonyl>-4,9,13-triazahexadecyl>carbamate
  参考文献：
  名称：

  Regioselective Deprotection and Acylation of Penta-N-Protected Thermopentamine

  摘要：

  The synthesis of the penta-N-protected polyamide 1 (ten-butyl N-{9-allyl-16-azido-13-(trinuoroacetyl)-4-[2-(trimethylsilyl)ethylsulfonyl]-4,9,13-triazahexadecyl]carbamate = tert-butyl N-{3-{[4-{allyl[3-[(3-azidopropyl)(trifluoroacetyl)aminopropyl}amino}butyl}{[2-(trimethylsilyl)ethyl]sulfonyl}amino}propyl}carbamate) is described, a derivative of thermopentamine (PA 3433) containing five independently removable amino-protecting groups. The selective deprotection of the five protecting groups used, it., of allyl, azido, (tert-butoxy)carbonyl (Boc). trifluoroacetyl, and [2-(trimethylsilyl)ethyl]sulfonyl (SES), as well as the rapid transamidation reaction of the trifluoroacetyl group yielding secondary amides is discussed. Subsequent acylation with 4-methoxycinnamoyl chloride at each N-atom of the pentamine backbone is achieved. For the acylation of the terminal N-atom the azido group is replaced by a (2,2,2-trichloro-1,l-dimethylethoxy)carbonyl (Tcboc) group.

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2300::aid-hlca2300>3.0.co;2-7