2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-L-rhamnopyranosylamine | 151962-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-L-rhamnopyranosylamine
• CAS: 151962-51-5
• 化学式: C₃₅H₃₅NO₁₁
• 分子量: 645.663
• InChiKey: NNHUBLMWMZNATE-ZZIKYNOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-L-rhamnopyranosylamine 在 氯 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,4-tri-O-benzoyl-β-L-rhamnopyranosylamine hydrochloride
  参考文献：
  名称：

  Tri-O-benzoyl-β-l-rhamnopyranosyl and β-l-fucopyranosyl isothiocyanates. Partially protected β-l-rhamnopyranosylenamines

  摘要：

  Regioselective benzoylations of N-(2,2-diethoxycarbonylvinyl)-beta-L-rhamnopyranosylamine (1) yielded 2,3-di-O- (3), 3,4-di-O- (4), and 3-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-beta-L-rhamnopyranosylamine (5) together with the tri-O-benzoylated derivative 2. Syntheses of 2,3,4-tri-O-benzoyl-beta-L-rhamno- (7) and -beta-L-fuco-pyranosyl isothiocyanate (13) from 2 and L-fucopyranosylamine, respectively, are described. N-Phenacyl-N'-(2,3,4-tri-O-benzoyl-beta-L-rhamno- (8) and -beta-L-fuco-pyranosylthiourea (14) were prepared from 7 and 13, respectively, by reaction with phenacylamine. Conformational properties and MS data of the prepared compounds are discussed.

  DOI：

  10.1016/0008-6215(93)84250-a
• 作为产物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-β-L-rhamnopyranosylamine 、 苯甲酰氯 在 吡啶 作用下， 反应 48.0h， 以70%的产率得到2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-L-rhamnopyranosylamine
  参考文献：
  名称：

  Tri-O-benzoyl-β-l-rhamnopyranosyl and β-l-fucopyranosyl isothiocyanates. Partially protected β-l-rhamnopyranosylenamines

  摘要：

  Regioselective benzoylations of N-(2,2-diethoxycarbonylvinyl)-beta-L-rhamnopyranosylamine (1) yielded 2,3-di-O- (3), 3,4-di-O- (4), and 3-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-beta-L-rhamnopyranosylamine (5) together with the tri-O-benzoylated derivative 2. Syntheses of 2,3,4-tri-O-benzoyl-beta-L-rhamno- (7) and -beta-L-fuco-pyranosyl isothiocyanate (13) from 2 and L-fucopyranosylamine, respectively, are described. N-Phenacyl-N'-(2,3,4-tri-O-benzoyl-beta-L-rhamno- (8) and -beta-L-fuco-pyranosylthiourea (14) were prepared from 7 and 13, respectively, by reaction with phenacylamine. Conformational properties and MS data of the prepared compounds are discussed.

  DOI：

  10.1016/0008-6215(93)84250-a