Methyl 2-[7-[bis(phenylmethoxycarbonylamino)methylideneamino]heptanoylamino]-2-hydroxyacetate | 189245-01-0

• 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: Methyl 2-[7-[bis(phenylmethoxycarbonylamino)methylideneamino]heptanoylamino]-2-hydroxyacetate
• CAS: 189245-01-0
• 化学式: C₂₇H₃₄N₄O₈
• 分子量: 542.589
• InChiKey: QHHKSUVIOURJGF-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Methyl 2-[7-[bis(phenylmethoxycarbonylamino)methylideneamino]heptanoylamino]-2-hydroxyacetate 在 吡啶 、 lithium hydroxide 、 二氯乙基铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.17h， 生成 (2S)-2-[7-[bis(phenylmethoxycarbonylamino)methylideneamino]heptanoylamino]-2-[(1R)-1-phenylethoxy]acetic acid
  参考文献：
  名称：

  Efficient synthesis of (S)-(−)- and (R)-(+)-enantiomers of 15-deoxyspergualin (15-DSG)

  摘要：

  An efficient synthesis of the (S)-(-)- and (R)-(+)-enantiomers of 15-deoxyspergualin (15-DSG) is reported. The synthesis involves preparative HPLC separation and subsequent hydrogenolysis of two diastereoisomers 10a and 10b of fully protected 15-DSG penultimates. Alternatively, diastereomerically pure amide 10b (97% de) was also prepared from acid 8b (97% de), which was obtained via crystallization of a 1:1 diastereomeric mixture of 8a and 8b. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00350-5
• 作为产物：
  描述：

  1,3-二(苄氧羰基)-2-甲基异硫脲 在 氨 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.0h， 生成 Methyl 2-[7-[bis(phenylmethoxycarbonylamino)methylideneamino]heptanoylamino]-2-hydroxyacetate
  参考文献：
  名称：

  Efficient synthesis of (S)-(−)- and (R)-(+)-enantiomers of 15-deoxyspergualin (15-DSG)

  摘要：

  An efficient synthesis of the (S)-(-)- and (R)-(+)-enantiomers of 15-deoxyspergualin (15-DSG) is reported. The synthesis involves preparative HPLC separation and subsequent hydrogenolysis of two diastereoisomers 10a and 10b of fully protected 15-DSG penultimates. Alternatively, diastereomerically pure amide 10b (97% de) was also prepared from acid 8b (97% de), which was obtained via crystallization of a 1:1 diastereomeric mixture of 8a and 8b. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00350-5

文献信息

• Stereoselective acetylation of racemic 7-[N,N′-bis-(benzyloxycarbonyl)-N-(guanidinoheptanoyl)]-α-hydroxyglycine
  作者：Ramesh N. Patel、Amit Banerjee、Laszlo J. Szarka

  DOI：10.1016/s0957-4166(97)00161-4

  日期：1997.6

  Chiral intermediate (-)-7-[N,N'-Bis(benzyloxycarbonyl)-N-(guanidino-heptanoyl)]-alpha-acetoxyglycine 2 was prepared for the total synthesis of a (-)-15 deoxyspergualin, an antitumor antibiotic and immunosuppressive agent. The stereoselective acetylation of racemic 7-[N,N'-Bis(benzyloxycarbonyl)-N-(guanidinoheptanoyl)]-alpha-hydroxyglycine 1 was carried out in methyl ethyl ketone (MEK) using lipase from Pseudomonas sp. (lipase AK). Vinyl acetate was used as an acylating agent. A reaction yield of 48% (theoretical max 50%) and an optical purity of 98% were obtained for S-(-)-acetate 2. The unreacted alcohol (+)-1 was obtained in 41% yield and 93.5% optical purity. (C) 1997 Elsevier Science Ltd.
• Total synthesis of (.+-.)-15-deoxyspergualin
  作者：Raymond J. Bergeron、James S. McManis

  DOI：10.1021/jo00385a010

  日期：1987.5
• Efficient synthesis of (S)-(−)- and (R)-(+)-enantiomers of 15-deoxyspergualin (15-DSG)
  作者：Xuebao Wang、John Thottathil

  DOI：10.1016/s0957-4166(00)00350-5

  日期：2000.9

  An efficient synthesis of the (S)-(-)- and (R)-(+)-enantiomers of 15-deoxyspergualin (15-DSG) is reported. The synthesis involves preparative HPLC separation and subsequent hydrogenolysis of two diastereoisomers 10a and 10b of fully protected 15-DSG penultimates. Alternatively, diastereomerically pure amide 10b (97% de) was also prepared from acid 8b (97% de), which was obtained via crystallization of a 1:1 diastereomeric mixture of 8a and 8b. (C) 2000 Elsevier Science Ltd. All rights reserved.