1-β-cyanolactose | 352432-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-β-cyanolactose
• CAS: 352432-83-8
• 化学式: C₁₃H₂₁NO₁₀
• 分子量: 351.31
• InChiKey: FZIXAJZNHXTUQQ-LEIWADKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.82
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  193.09
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-β-cyanolactose 在 4-二甲氨基吡啶 吡啶 作用下， 反应 8.0h， 生成 2,3,6,2',3',4',6'-hepta-O-acetyl-β-cyanolactose
  参考文献：
  名称：

  Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides

  摘要：

  [GRAPHICS]Reported herein is a general method for the efficient syntheses of a variety of beta -cyano glycosides through the activation of per-O-trimethylsllyl glycosides with TMSI to form alpha -glycosyl iodides, which undergo S(N)2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)(6) in THF/H2O to give the corresponding aminomethyl glycosides.

  DOI：

  10.1021/ol0160405
• 作为产物：
  描述：

  在 甲醇 作用下， 反应 0.67h， 生成 1-β-cyanolactose
  参考文献：
  名称：

  Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides

  摘要：

  [GRAPHICS]Reported herein is a general method for the efficient syntheses of a variety of beta -cyano glycosides through the activation of per-O-trimethylsllyl glycosides with TMSI to form alpha -glycosyl iodides, which undergo S(N)2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)(6) in THF/H2O to give the corresponding aminomethyl glycosides.

  DOI：

  10.1021/ol0160405