[(2S,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-2-(acetylsulfanylmethyl)-6-prop-2-enoxyoxan-3-yl] 2-(azidomethyl)benzoate | 165805-40-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-2-(acetylsulfanylmethyl)-6-prop-2-enoxyoxan-3-yl] 2-(azidomethyl)benzoate
• CAS: 165805-40-3
• 化学式: C₂₃H₂₈N₄O₈S
• 分子量: 520.563
• InChiKey: URARKTBACLPUFH-GJTYKATRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-2-(acetylsulfanylmethyl)-6-prop-2-enoxyoxan-3-yl] 2-(azidomethyl)benzoate 在 三(4-甲氧苯基)膦 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 1.5h， 以81%的产率得到Acetic acid (2S,3R,4R,5S,6S)-3-acetylamino-6-acetylsulfanylmethyl-2-allyloxy-5-hydroxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Regiospecific 4,6-Functionalization of Pyranosides via Dimethylboron Bromide-Mediated Cleavage of Phthalide Orthoesters

  摘要：

  An efficient strategy for regiocontrolled differentiation of the 4,6-positions of pyranosides has been developed using dimethylboron bromide-mediated cleavage of phthalide orthoesters. The reaction proceeds under mild conditions, is tolerant of additional acetal functionality, and produces a benzoate bearing suitable functionality for intramolecular assisted cleavage in the presence of SAc, OAc, and NHAc groups.

  DOI：

  10.1021/ja00106a021
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 二甲基溴化硼 、 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 、 tetramethylguanidinum azide 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 [(2S,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-2-(acetylsulfanylmethyl)-6-prop-2-enoxyoxan-3-yl] 2-(azidomethyl)benzoate
  参考文献：
  名称：

  Regiospecific 4,6-Functionalization of Pyranosides via Dimethylboron Bromide-Mediated Cleavage of Phthalide Orthoesters

  摘要：

  An efficient strategy for regiocontrolled differentiation of the 4,6-positions of pyranosides has been developed using dimethylboron bromide-mediated cleavage of phthalide orthoesters. The reaction proceeds under mild conditions, is tolerant of additional acetal functionality, and produces a benzoate bearing suitable functionality for intramolecular assisted cleavage in the presence of SAc, OAc, and NHAc groups.

  DOI：

  10.1021/ja00106a021