benzyl (3R)-3-<<(3'R)-3'-<<2-<<(tert-butoxy)carbonyl>amino>acetyl>oxy>butanoyl>oxy>butanoate | 220459-14-3

• 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: benzyl (3R)-3-<<(3'R)-3'-<<2-<<(tert-butoxy)carbonyl>amino>acetyl>oxy>butanoyl>oxy>butanoate
• CAS: 220459-14-3
• 化学式: C₂₂H₃₁NO₈
• 分子量: 437.49
• InChiKey: YIKIOUIZMKQEMT-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl (3R)-3-<<(3'R)-3'-<<2-<<(tert-butoxy)carbonyl>amino>acetyl>oxy>butanoyl>oxy>butanoate 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 benzyl (3R)-3-<<(3'R)-3'-<<2-<<5-<(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno<3,4-d>imidazol-4-yl>pentanoyl>amino>acetyl>oxy>butanoyl>oxy>butanoate
  参考文献：
  名称：

  Synthesis of Amino-Acid-, Carbohydrate-, Coumarin-, and Biotin-Labelled Oligo[(R)-3-Hydroxybutanoic Acids] (OHB)

  摘要：

  The benzyl esters 1-3 of oligo[(R)-3-hydroxybutanoic acids] (OHB) containing 2, 16, or 32 IIB units were coupled at the hydroxy terminus with arginine (by esterification with carbodiimide), with glucose (by acetalization with glucosyl trichloroacetimidate), and with 7-(dimethylamino)coumarin-4-acetic acid and biotin (by amide: formation through a glycine: linker) to give. after deprotection(s),the corresponding 'labelled' OHB acids 7-9, 12, 13, 25, 26, 33, and 34 (Schemes 1, 4, and 5). The respective novel 16- and 32mer derivatives exhibit distinct water solubility (Table) or may be detected (in minute amounts) by fluorescence spectroscopy, properties required for biochemical investigations.

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2414::aid-hlca2414>3.0.co;2-c
• 作为产物：
  描述：

  BOC-甘氨酸 、 (R)-(-)-2-benzyloxycarbonyl-1-methylethyl (R)-(-)-3-hydroxybutyrate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到benzyl (3R)-3-<<(3'R)-3'-<<2-<<(tert-butoxy)carbonyl>amino>acetyl>oxy>butanoyl>oxy>butanoate
  参考文献：
  名称：

  Synthesis of Amino-Acid-, Carbohydrate-, Coumarin-, and Biotin-Labelled Oligo[(R)-3-Hydroxybutanoic Acids] (OHB)

  摘要：

  The benzyl esters 1-3 of oligo[(R)-3-hydroxybutanoic acids] (OHB) containing 2, 16, or 32 IIB units were coupled at the hydroxy terminus with arginine (by esterification with carbodiimide), with glucose (by acetalization with glucosyl trichloroacetimidate), and with 7-(dimethylamino)coumarin-4-acetic acid and biotin (by amide: formation through a glycine: linker) to give. after deprotection(s),the corresponding 'labelled' OHB acids 7-9, 12, 13, 25, 26, 33, and 34 (Schemes 1, 4, and 5). The respective novel 16- and 32mer derivatives exhibit distinct water solubility (Table) or may be detected (in minute amounts) by fluorescence spectroscopy, properties required for biochemical investigations.

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2414::aid-hlca2414>3.0.co;2-c