t-butyl (2S,4R)-5-azido-2-N-(9-phenyl-9H-fluoren-9-yl)amino-4-N-(2-trimethylsilylethanesulfonyl)aminopentanoate | 743442-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: t-butyl (2S,4R)-5-azido-2-N-(9-phenyl-9H-fluoren-9-yl)amino-4-N-(2-trimethylsilylethanesulfonyl)aminopentanoate
• 英文别名: tert-butyl (2S,4R)-5-azido-2-[(9-phenylfluoren-9-yl)amino]-4-(2-trimethylsilylethylsulfonylamino)pentanoate
• CAS: 743442-79-7
• 化学式: C₃₃H₄₃N₅O₄SSi
• 分子量: 633.887
• InChiKey: CWCXIRPZGCYDKU-RNAHPLFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  t-butyl (2S,4R)-5-azido-2-N-(9-phenyl-9H-fluoren-9-yl)amino-4-N-(2-trimethylsilylethanesulfonyl)aminopentanoate 在 水 、 三乙胺 、 三苯基膦 、 mercury dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 104.0h， 生成 t-butyl (2S,4R)-5-[N',N''-bis(benzyloxycarbonyl)guanidino]-2-N-(9-phenyl-9H-fluoren-9-yl)amino-4-N-(2-trimethylsilylethanesulfonyl)aminopentanoate
  参考文献：
  名称：

  Iminoiodane mediated aziridination of α-allylglycine: access to a novel rigid arginine derivative and to the natural amino acid enduracididine

  摘要：

  The synthesis of fully protected ammodihydrohistidines in optically pure form is described starting from allylglycine derivatives. These compounds represent novel conformationally constrained analogues of arginine, one of them being, in addition, a protected form of the marine natural product, enduracididine. The key step of the strategy is a one-pot copper-catalyzed aziridination of t-butyl (S)-N-(9-phenyl-9H-fluoren-9-yl)allylglycinate ((S)-16) with 2-trimethylsilylethanesulfonamide in the presence of iodosylbenzene. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.05.034
• 作为产物：
  描述：

  9-溴-9-苯基芴 在 三甲基氯硅烷 、 sodium azide 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 亚碘酰苯 、 3 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 238.0h， 生成 t-butyl (2S,4R)-5-azido-2-N-(9-phenyl-9H-fluoren-9-yl)amino-4-N-(2-trimethylsilylethanesulfonyl)aminopentanoate
  参考文献：
  名称：

  Iminoiodane mediated aziridination of α-allylglycine: access to a novel rigid arginine derivative and to the natural amino acid enduracididine

  摘要：

  The synthesis of fully protected ammodihydrohistidines in optically pure form is described starting from allylglycine derivatives. These compounds represent novel conformationally constrained analogues of arginine, one of them being, in addition, a protected form of the marine natural product, enduracididine. The key step of the strategy is a one-pot copper-catalyzed aziridination of t-butyl (S)-N-(9-phenyl-9H-fluoren-9-yl)allylglycinate ((S)-16) with 2-trimethylsilylethanesulfonamide in the presence of iodosylbenzene. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.05.034

文献信息

• Iminoiodane mediated aziridination of α-allylglycine: access to a novel rigid arginine derivative and to the natural amino acid enduracididine
  作者：Laurent Sanière、Loı̈c Leman、Jean-Jacques Bourguignon、Philippe Dauban、Robert H Dodd

  DOI：10.1016/j.tet.2004.05.034

  日期：2004.7

  The synthesis of fully protected ammodihydrohistidines in optically pure form is described starting from allylglycine derivatives. These compounds represent novel conformationally constrained analogues of arginine, one of them being, in addition, a protected form of the marine natural product, enduracididine. The key step of the strategy is a one-pot copper-catalyzed aziridination of t-butyl (S)-N-(9-phenyl-9H-fluoren-9-yl)allylglycinate ((S)-16) with 2-trimethylsilylethanesulfonamide in the presence of iodosylbenzene. (C) 2004 Published by Elsevier Ltd.