[(1R,3S,7R,8S,9S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxa-2-thiatricyclo[7.4.0.03,7]tridecan-8-yl] 2-(azidomethyl)benzoate | 501432-20-8

• 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: [(1R,3S,7R,8S,9S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxa-2-thiatricyclo[7.4.0.03,7]tridecan-8-yl] 2-(azidomethyl)benzoate
• CAS: 501432-20-8
• 化学式: C₂₀H₂₅N₃O₆S
• 分子量: 435.501
• InChiKey: IZNWYLVQFOOUQH-QFXBJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(1R,3S,7R,8S,9S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxa-2-thiatricyclo[7.4.0.03,7]tridecan-8-yl] 2-(azidomethyl)benzoate 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以97%的产率得到1,2:4,6-di-O-isopropylidene-5-thio-α-D-glucopyranose
  参考文献：
  名称：

  NOVEL PREPARATION OF (2-AZIDOMETHYL)BENZOIC ACID AND AN APPLICATION AS A PROTECTIVE GROUP

  摘要：

  A novel preparation method of 2-(azidomethyl) benzoic acid, a precursor of (2-azidomethyl)benzoyl (AZMB) protective group, was developed which can provide pure sample in gram scale without chromatographic purifications. Reductive cleavage using triphenylphosphine was found to be effective in the case of sterically hindered ester that resists under basic hydrolysis.

  DOI：

  10.1081/scc-120014042
• 作为产物：
  描述：

  2-氯甲基苯甲酸甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 氯化亚砜 、 sodium azide 、 potassium acetate 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 74.0h， 生成 [(1R,3S,7R,8S,9S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxa-2-thiatricyclo[7.4.0.03,7]tridecan-8-yl] 2-(azidomethyl)benzoate
  参考文献：
  名称：

  NOVEL PREPARATION OF (2-AZIDOMETHYL)BENZOIC ACID AND AN APPLICATION AS A PROTECTIVE GROUP

  摘要：

  A novel preparation method of 2-(azidomethyl) benzoic acid, a precursor of (2-azidomethyl)benzoyl (AZMB) protective group, was developed which can provide pure sample in gram scale without chromatographic purifications. Reductive cleavage using triphenylphosphine was found to be effective in the case of sterically hindered ester that resists under basic hydrolysis.

  DOI：

  10.1081/scc-120014042

文献信息

• NOVEL PREPARATION OF (2-AZIDOMETHYL)BENZOIC ACID AND AN APPLICATION AS A PROTECTIVE GROUP
  作者：Hiroko Matsuda、Masaru Hashimoto、Toshikatsu Okuno

  DOI：10.1081/scc-120014042

  日期：2002.1

  A novel preparation method of 2-(azidomethyl) benzoic acid, a precursor of (2-azidomethyl)benzoyl (AZMB) protective group, was developed which can provide pure sample in gram scale without chromatographic purifications. Reductive cleavage using triphenylphosphine was found to be effective in the case of sterically hindered ester that resists under basic hydrolysis.