2-[(S)-1-({2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-ethyl]-thiazole-4-carbonyl}-amino)-ethyl]-thiazole-4-carboxylic acid allyl ester | 851790-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-[(S)-1-({2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-ethyl]-thiazole-4-carbonyl}-amino)-ethyl]-thiazole-4-carboxylic acid allyl ester
• 英文别名: prop-2-enyl 2-[(1S)-1-[[2-[(1S)-1-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]-1,3-thiazole-4-carbonyl]amino]ethyl]-1,3-thiazole-4-carboxylate
• CAS: 851790-98-2
• 化学式: C₃₀H₂₈N₄O₅S₂
• 分子量: 588.708
• InChiKey: NDBCQTAIBPETDT-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  119.51
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-[(S)-1-({2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-ethyl]-thiazole-4-carbonyl}-amino)-ethyl]-thiazole-4-carboxylic acid allyl ester 在 4-二甲氨基吡啶 、 palladium diacetate 、 styrene polymer-PPh₃ 、 苯硅烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.75h， 生成 (4S,11S,14S,17S)-11-Benzyl-4,17-dimethyl-14-((R)-1-trityloxy-ethyl)-6,19-dithia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetraone
  参考文献：
  名称：

  Total synthesis of didmolamides A and B

  摘要：

  The first total synthesis of didmolamides A (1) and B (2) has been accomplished by the solid phase assembly of thiazole-containing amino acids and commercially available Fmoc-protected amino acids. The synthesis of didmolamide B was also achieved in high yield using solution phase peptide synthesis. The thiazole-containing amino acid composing 1 and 2 was synthesized by a MnO2 oxidation of a thiazoline, prepared from an Ala-Cys dipeptide using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate. The final macrolactamization was accomplished efficiently by PyBOP and DMAP in solution. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.097
• 作为产物：
  描述：

  Fmoc-Cys[Trt]-OAllyl 在 manganese(IV) oxide 、 三氟甲磺酸酐 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 、 三苯基氧化膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.0h， 生成 2-[(S)-1-({2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-ethyl]-thiazole-4-carbonyl}-amino)-ethyl]-thiazole-4-carboxylic acid allyl ester
  参考文献：
  名称：

  Total synthesis of didmolamides A and B

  摘要：

  The first total synthesis of didmolamides A (1) and B (2) has been accomplished by the solid phase assembly of thiazole-containing amino acids and commercially available Fmoc-protected amino acids. The synthesis of didmolamide B was also achieved in high yield using solution phase peptide synthesis. The thiazole-containing amino acid composing 1 and 2 was synthesized by a MnO2 oxidation of a thiazoline, prepared from an Ala-Cys dipeptide using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate. The final macrolactamization was accomplished efficiently by PyBOP and DMAP in solution. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.097