2-(2-{[2-(2-{2-[(2-tert-butoxycarbonylamino-3-methylpentanoyl)methylamino]acetoxy}-3-phenyl-propionylamino)-3-methylpentanoyl]methylamino}acetoxy)-3-phenylpropionic acid benzyl ester | 858972-92-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2-{[2-(2-{2-[(2-tert-butoxycarbonylamino-3-methylpentanoyl)methylamino]acetoxy}-3-phenyl-propionylamino)-3-methylpentanoyl]methylamino}acetoxy)-3-phenylpropionic acid benzyl ester
• 英文别名: Boc-aIle-Sar-D-OPhe-aIle-Sar-D-OPhe-OBn；benzyl (2R)-2-[2-[methyl-[(2S,3R)-3-methyl-2-[[(2R)-2-[2-[methyl-[(2S,3R)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]acetyl]oxy-3-phenylpropanoyl]amino]pentanoyl]amino]acetyl]oxy-3-phenylpropanoate
• CAS: 858972-92-6
• 化学式: C₄₈H₆₄N₄O₁₁
• 分子量: 873.056
• InChiKey: VXUXSXHFUIHELS-GVENUREPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  63
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  187
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(2-{[2-(2-{2-[(2-tert-butoxycarbonylamino-3-methylpentanoyl)methylamino]acetoxy}-3-phenyl-propionylamino)-3-methylpentanoyl]methylamino}acetoxy)-3-phenylpropionic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 (R)-2-(2-{[(2S,3R)-2-((R)-2-{2-[((2S,3R)-2-Amino-3-methyl-pentanoyl)-methyl-amino]-acetoxy}-3-phenyl-propionylamino)-3-methyl-pentanoyl]-methyl-amino}-acetoxy)-3-phenyl-propionic acid; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Total synthesis of hirsutellide A

  摘要：

  The total synthesis of hirsutellide A 1 was described. The linear hexadepsipeptide precursor 2 was synthesized in 45%, yield from N'-Boc-Me-Gly by three coupling reactions with DCC, HATU and BOP-Cl, respectively. Macrocyclization was successfully performed on the fully deprotected amino acid 14 with BOP-Cl in 15%, yield and with FDDP in 22% yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.087
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 2-(2-{[2-(2-{2-[(2-tert-butoxycarbonylamino-3-methylpentanoyl)methylamino]acetoxy}-3-phenyl-propionylamino)-3-methylpentanoyl]methylamino}acetoxy)-3-phenylpropionic acid benzyl ester
  参考文献：
  名称：

  Total synthesis of hirsutellide A

  摘要：

  The total synthesis of hirsutellide A 1 was described. The linear hexadepsipeptide precursor 2 was synthesized in 45%, yield from N'-Boc-Me-Gly by three coupling reactions with DCC, HATU and BOP-Cl, respectively. Macrocyclization was successfully performed on the fully deprotected amino acid 14 with BOP-Cl in 15%, yield and with FDDP in 22% yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.087

文献信息

• Synthesis of the Key Precursor of Hirsutellide A
  作者：Yanjie Xu、Xuemin Duan、Meiling Li、Liqin Jiang、Guangle Zhao、Yi Meng、Ligong Chen

  DOI：10.3390/10010259

  日期：——

  Hexadepsipeptide 2, the precursor of Hirsutellide A (1), was synthesized in an overall yield of 45% from N-Boc-Me-Gly via three coupling reactions using dicyclohexylcarbodiimide (DCC), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyl- uronium hexafluorophosphate (HATU) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl), respectively.

  通过使用二环己基碳二亚胺 (DCC)、O-(7-氮杂苯并三唑-1-基) 的三个偶联反应，从 N-Boc-Me-Gly 以 45% 的总产率合成了六肽 2，即 Hirsutellide A (1) 的前体-N,N,N',N'-四甲基-六氟磷酸脲 (HATU) 和双 (2-oxo-3-oxazolidinyl) 次膦酰氯 (BOP-Cl)。