phenyl cyanomethyl 2',4'-di-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-(1->6)-(2,3,4-tri-O-acetyl-β-D-glucopyranoside) | 1055037-22-3

• 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: phenyl cyanomethyl 2',4'-di-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-(1->6)-(2,3,4-tri-O-acetyl-β-D-glucopyranoside)
• 英文别名: [(2R,3R,4S,5R,6R)-5-acetyloxy-4-hydroxy-2-(phenylmethoxymethyl)-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(R)-cyano(phenyl)methoxy]oxan-2-yl]methoxy]oxan-3-yl] acetate
• CAS: 1055037-22-3
• 化学式: C₃₇H₄₃NO₁₆
• 分子量: 757.746
• InChiKey: ADKZUWZCHRGEGY-JFYMAFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  54
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  222
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  phenyl cyanomethyl 2',4'-di-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-(1->6)-(2,3,4-tri-O-acetyl-β-D-glucopyranoside) 在 palladium on activated charcoal Amberlite IRA-400 resin (OH^- form) 、 1,3-环己二烯 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 9.5h， 生成 别乳糖
  参考文献：
  名称：

  The Synthesis of Allolactose from Amygdalin

  摘要：

  An original synthetic approach to the disaccharide allolactose (1) starting from the natural glycoside amygdalin (2) has been developed. The disaccharidic gentiobiose unit present in 2 has been transformed into the allolactose moiety using a four step protocol based on the selective inversion of the C-4' OH. The efficient removal of the natural benzylic aglycone (a mandelonitrile moiety) was accomplished by catalytic transfer hydrogenolysis. The behavior of allolactose with different enzymes is also described.

  DOI：

  10.1081/car-120023469
• 作为产物：
  描述：

  2,3,4,2',3'-penta-O-acetyl-6'-O-benzyl amygdalin 在 吡啶 、 三氟甲磺酸酐 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以67%的产率得到phenyl cyanomethyl 2',4'-di-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-(1->6)-(2,3,4-tri-O-acetyl-β-D-glucopyranoside)
  参考文献：
  名称：

  The Synthesis of Allolactose from Amygdalin

  摘要：

  An original synthetic approach to the disaccharide allolactose (1) starting from the natural glycoside amygdalin (2) has been developed. The disaccharidic gentiobiose unit present in 2 has been transformed into the allolactose moiety using a four step protocol based on the selective inversion of the C-4' OH. The efficient removal of the natural benzylic aglycone (a mandelonitrile moiety) was accomplished by catalytic transfer hydrogenolysis. The behavior of allolactose with different enzymes is also described.

  DOI：

  10.1081/car-120023469

文献信息

• The Synthesis of Allolactose from Amygdalin
  作者：Davide Prosperi、Luigi Panza、Dietmar Haltrich、Micol Nonini、Sergio Riva

  DOI：10.1081/car-120023469

  日期：2003.1.8

  An original synthetic approach to the disaccharide allolactose (1) starting from the natural glycoside amygdalin (2) has been developed. The disaccharidic gentiobiose unit present in 2 has been transformed into the allolactose moiety using a four step protocol based on the selective inversion of the C-4' OH. The efficient removal of the natural benzylic aglycone (a mandelonitrile moiety) was accomplished by catalytic transfer hydrogenolysis. The behavior of allolactose with different enzymes is also described.