benzyl N-[(1R)-2-benzylsulfanyl-1-[5-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-phenylethyl]sulfanyl-1,3,4-oxadiazol-2-yl]ethyl]carbamate | 1360471-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: benzyl N-[(1R)-2-benzylsulfanyl-1-[5-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-phenylethyl]sulfanyl-1,3,4-oxadiazol-2-yl]ethyl]carbamate
• CAS: 1360471-00-6
• 化学式: C₄₂H₃₈N₄O₅S₂
• 分子量: 742.92
• InChiKey: CFLHIDIZWLHUDC-AMAPPZPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Fmoc-Phg-ψ[CH2I] 、 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以71%的产率得到benzyl N-[(1R)-2-benzylsulfanyl-1-[5-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-phenylethyl]sulfanyl-1,3,4-oxadiazol-2-yl]ethyl]carbamate
  参考文献：
  名称：

  A facile one-pot synthesis of Nα-Z/Boc-protected S-linked 1,3,4-oxadiazole tethered peptidomimetics

  摘要：

  A new class of S-linked 1,3,4-oxadiazole-tethered N-alpha-protected peptidomimetics is designed and synthesized by a reaction of N-alpha-Z/Boc-protected 1,3,4-oxadiazole-2-thiol with alpha-bromo ester derived from amino acid. The protocol has also been employed for the synthesis of glycosylated amino acids and N,N'-orthogonally protected dipeptidomimetics bearing S-linked 1,3,4-oxadiazole mimetics as well. The intermediate 5-alkyl amino-1,3,4-oxadiazole-2-thiols have been isolated as stable compounds. Further, the chain extension at both N- and C-termini of N-protected S-linked 1,3,4-oxadiazole tethered dipeptidomimetics was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.093

文献信息

• A facile one-pot synthesis of Nα-Z/Boc-protected S-linked 1,3,4-oxadiazole tethered peptidomimetics
  作者：Vommina V. Sureshbabu、B. Vasantha、G. Nagendra

  DOI：10.1016/j.tetlet.2011.12.093

  日期：2012.3

  A new class of S-linked 1,3,4-oxadiazole-tethered N-alpha-protected peptidomimetics is designed and synthesized by a reaction of N-alpha-Z/Boc-protected 1,3,4-oxadiazole-2-thiol with alpha-bromo ester derived from amino acid. The protocol has also been employed for the synthesis of glycosylated amino acids and N,N'-orthogonally protected dipeptidomimetics bearing S-linked 1,3,4-oxadiazole mimetics as well. The intermediate 5-alkyl amino-1,3,4-oxadiazole-2-thiols have been isolated as stable compounds. Further, the chain extension at both N- and C-termini of N-protected S-linked 1,3,4-oxadiazole tethered dipeptidomimetics was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.