2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propyl]-5-methyl-oxazole-4-carboxylic acid benzyl ester | 831239-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propyl]-5-methyl-oxazole-4-carboxylic acid benzyl ester
• 英文别名: benzyl 2-[(1S)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylpropyl]-5-methyl-1,3-oxazole-4-carboxylate
• CAS: 831239-00-0
• 化学式: C₃₁H₃₀N₂O₅
• 分子量: 510.59
• InChiKey: ZZIPHUPYUJUOPC-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propyl]-5-methyl-oxazole-4-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2-[(S)-1-({2-[(S)-1-({2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propyl]-5-methyl-oxazole-4-carbonyl}-amino)-2-methyl-propyl]-oxazole-4-carbonyl}-amino)-2-methyl-propyl]-thiazole-4-carboxylic acid allyl ester
  参考文献：
  名称：

  The total synthesis of bistratamides F–I

  摘要：

  The total synthesis of bistratamides F-I (2-5) have been achieved in overall yields of 3, 10, 13, and 27%, respectively. The thiazole substructure was prepared utilizing a MnO2 oxidation of a thiazoline, synthesized from a Val-Cys dipeptide using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate. The serine-based oxazole substructure was prepared from a Val-Ser dipeptide using literature methods. The threonine-derived oxazole substructure was synthesized from a ketoamide dipeptide using the bisphosphonium salt employed for thiazoline preparation. Most of the amide bonds were formed using HBTU and HOBt in the presence of DIEA. The final macrocyclization step was accomplished efficiently by PyBOP and DMAP in all cases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.024
• 作为产物：
  描述：

  (2S,3R)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyrylamino]-3-hydroxy-butyric acid benzyl ester 在 三氟甲磺酸酐 、 戴斯-马丁氧化剂 、 三苯基氧化膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propyl]-5-methyl-oxazole-4-carboxylic acid benzyl ester
  参考文献：
  名称：

  The total synthesis of bistratamides F–I

  摘要：

  The total synthesis of bistratamides F-I (2-5) have been achieved in overall yields of 3, 10, 13, and 27%, respectively. The thiazole substructure was prepared utilizing a MnO2 oxidation of a thiazoline, synthesized from a Val-Cys dipeptide using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate. The serine-based oxazole substructure was prepared from a Val-Ser dipeptide using literature methods. The threonine-derived oxazole substructure was synthesized from a ketoamide dipeptide using the bisphosphonium salt employed for thiazoline preparation. Most of the amide bonds were formed using HBTU and HOBt in the presence of DIEA. The final macrocyclization step was accomplished efficiently by PyBOP and DMAP in all cases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.024

文献信息

• The total synthesis of bistratamides F–I
  作者：Shu-Li You、Jeffery W. Kelly

  DOI：10.1016/j.tet.2004.10.024

  日期：2005.1

  The total synthesis of bistratamides F-I (2-5) have been achieved in overall yields of 3, 10, 13, and 27%, respectively. The thiazole substructure was prepared utilizing a MnO2 oxidation of a thiazoline, synthesized from a Val-Cys dipeptide using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate. The serine-based oxazole substructure was prepared from a Val-Ser dipeptide using literature methods. The threonine-derived oxazole substructure was synthesized from a ketoamide dipeptide using the bisphosphonium salt employed for thiazoline preparation. Most of the amide bonds were formed using HBTU and HOBt in the presence of DIEA. The final macrocyclization step was accomplished efficiently by PyBOP and DMAP in all cases. (C) 2004 Elsevier Ltd. All rights reserved.