tert-butyl N-<3-<(4-bromobutyl)<<2-(trimethylsilyl)ethyl>sulfonyl>amino>propyl>carbamate | 211623-85-7

• 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-<3-<(4-bromobutyl)<<2-(trimethylsilyl)ethyl>sulfonyl>amino>propyl>carbamate
• 英文别名: tert-butyl N-[N'-(4-bromobutyl)-N'-(trimethylsilylethanesulfonyl)-3-aminoprop-1-yl]carbamate；tert-butyl N-[3-[4-bromobutyl(2-trimethylsilylethylsulfonyl)amino]propyl]carbamate
• CAS: 211623-85-7
• 化学式: C₁₇H₃₇BrN₂O₄SSi
• 分子量: 473.547
• InChiKey: FUOJMJZXOCDCRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-<3-<(4-bromobutyl)<<2-(trimethylsilyl)ethyl>sulfonyl>amino>propyl>carbamate 在 potassium fluoride 、 Celite 、 水 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 sodium hydroxide 、 乙醚 、 水 、 甲苯 、 乙腈 为溶剂， 反应 238.5h， 生成 tert-butyl N-<9-allyl-16-amino-13-<(2,2,2-trichloro-1,1-dimethylethoxy)carbonyl>-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：

  2-(三甲基硅基)乙烷磺酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 30.5h， 生成 tert-butyl N-<3-<(4-bromobutyl)<<2-(trimethylsilyl)ethyl>sulfonyl>amino>propyl>carbamate
  参考文献：
  名称：

  Synthesis of penta-N-protected thermopentamine and its selective deprotection

  摘要：

  DOI：

  10.1016/s0040-4020(98)00442-6

文献信息

• Regioselective Deprotection and Acylation of Penta-N-Protected Thermopentamine
  作者：Jae Kyoung Pak、Manfred Hesse

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

  日期：1998.12.16

  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.
• Synthesis of penta-N-protected thermopentamine and its selective deprotection
  作者：Jae Kyoung Pak、Armin Guggisberg、Manfred Hesse

  DOI：10.1016/s0040-4020(98)00442-6

  日期：1998.7