N,N′-(bis-Cbz-guanidino)heptanoic acid | 189245-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N′-(bis-Cbz-guanidino)heptanoic acid
• 英文别名: 7-[Bis(phenylmethoxycarbonylamino)methylideneamino]heptanoic acid
• CAS: 189245-00-9
• 化学式: C₂₄H₂₉N₃O₆
• 分子量: 455.511
• InChiKey: XYCNQCZBMJNOFJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N′-(bis-Cbz-guanidino)heptanoic acid 在 氨 、 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 38.0h， 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
• 作为产物：
  描述：

  1,3-二(苄氧羰基)-2-甲基异硫脲 、 7-氨基庚酸 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以81%的产率得到N,N′-(bis-Cbz-guanidino)heptanoic 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

文献信息

• Preparation of optically active (S)-(-) and (R)-(+)- deoxyspergualin and novel intermediates thereof
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0765866A2

  公开（公告）日：1997-04-02

  A process for preparing optically active (S)-(-) and (R)-(+)-deoxyspergualin and salts thereof of the formula I by reacting a compound of formula II with a compound of formula III in the presence of a condensing/dehydrating agent and an organic or inorganic base in an organic solvent to form a compound of formula IV which can then be converted to the desired final product of formula I via deprotection and hydrogenolysis. The invention also comprises the compounds of the formula II, IV and VII

  一种制备光学活性(S)-(-)和(R)-(+)-脱氧表阿胶及其式 I 盐的工艺 使式 II 的化合物与式 III 的化合物反应 与式 III 的化合物反应 在冷凝剂/脱水剂和有机或无机碱存在下，在有机溶剂中反应生成式 IV 化合物 然后通过脱保护和氢解将其转化为所需的式 I 最终产物。本发明还包括式 II、IV 和 VII 的化合物
• Design and synthesis of 15-deoxyspergualin–biotin conjugates as novel binding probes for target protein screening
  作者：Masahiko Morioka、Kuniki Kato、Kazuo Umezawa

  DOI：10.1038/ja.2016.32

  日期：2016.7
• 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.