7-[N,N'-bis(benzyloxycarbonyl)guanidino]heptanoyl-(RS)-2-[(R)-sec-phenethoxy]glycine methyl ester | 189245-02-1

• 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: 7-[N,N'-bis(benzyloxycarbonyl)guanidino]heptanoyl-(RS)-2-[(R)-sec-phenethoxy]glycine methyl ester
• 英文别名: methyl 2-[7-[bis(phenylmethoxycarbonylamino)methylideneamino]heptanoylamino]-2-[(1R)-1-phenylethoxy]acetate
• CAS: 189245-02-1
• 化学式: C₃₅H₄₂N₄O₈
• 分子量: 646.74
• InChiKey: PKMIHOSLLJYHCR-SYQKMTEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  47
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  154
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-[N,N'-bis(benzyloxycarbonyl)guanidino]heptanoyl-(RS)-2-[(R)-sec-phenethoxy]glycine methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以50%的产率得到(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 吡啶 、 氨 、 二氯乙基铝 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 61.17h， 生成 7-[N,N'-bis(benzyloxycarbonyl)guanidino]heptanoyl-(RS)-2-[(R)-sec-phenethoxy]glycine methyl ester
  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

• 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.