methyl 2-[(2R,3S,4S,5R,6R)-6-[(2S,3S)-3-[(2S,3S)-5-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-methoxypentyl]oxiran-2-yl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate | 945037-22-9

• 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: methyl 2-[(2R,3S,4S,5R,6R)-6-[(2S,3S)-3-[(2S,3S)-5-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-methoxypentyl]oxiran-2-yl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate
• CAS: 945037-22-9
• 化学式: C₃₆H₆₄O₁₀SSi₂
• 分子量: 745.135
• InChiKey: FKWURAGMAGIWRB-BXXMCOKASA-N

物化性质

• 沸点：
  715.8±60.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2R,3S,4S,5R,6R)-6-[(2S,3S)-3-[(2S,3S)-5-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-methoxypentyl]oxiran-2-yl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate 在 tin(ll) chloride 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以80%的产率得到methyl 2-[(2R,3S,4S,5R,6R)-6-[(4S,5R)-5-[(2S,3S)-5-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-methoxypentyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate
  参考文献：
  名称：

  Lactol-Directed Osmylation. Stereodivergent Synthesis of Four C-19,20 Apoptolidin Diols from a Single Allylic Hemiacetal

  摘要：

  A synthetic approach to prepare four Apoptolidin C-19,20 diastereomeric diol derivatives was developed. Two diastereomers were obtained from the (Z)-form, which is converted to the (E)-form, followed by dihydroxylation to deliver two more diastereomers. The (E)-allylic hemiacetal and methoxyacetal showed opposite diastereoselectivity.

  DOI：

  10.1021/ol0707564
• 作为产物：
  描述：

  methyl 2-[(2R,3S,4S,5R,6S)-6-[(Z,4S,5S)-7-(benzenesulfonyl)-5-[tert-butyl(dimethyl)silyl]oxy-4-methoxyhept-1-enyl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate 在 二甲基二环氧乙烷 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 methyl 2-[(2R,3S,4S,5R,6R)-6-[(2S,3S)-3-[(2S,3S)-5-(benzenesulfonyl)-3-[tert-butyl(dimethyl)silyl]oxy-2-methoxypentyl]oxiran-2-yl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate
  参考文献：
  名称：

  Lactol-Directed Osmylation. Stereodivergent Synthesis of Four C-19,20 Apoptolidin Diols from a Single Allylic Hemiacetal

  摘要：

  A synthetic approach to prepare four Apoptolidin C-19,20 diastereomeric diol derivatives was developed. Two diastereomers were obtained from the (Z)-form, which is converted to the (E)-form, followed by dihydroxylation to deliver two more diastereomers. The (E)-allylic hemiacetal and methoxyacetal showed opposite diastereoselectivity.

  DOI：

  10.1021/ol0707564

文献信息

• Lactol-Directed Osmylation. Stereodivergent Synthesis of Four C-19,20 Apoptolidin Diols from a Single Allylic Hemiacetal
  作者：Youngsoon Kim、Philip L. Fuchs

  DOI：10.1021/ol0707564

  日期：2007.6.1

  A synthetic approach to prepare four Apoptolidin C-19,20 diastereomeric diol derivatives was developed. Two diastereomers were obtained from the (Z)-form, which is converted to the (E)-form, followed by dihydroxylation to deliver two more diastereomers. The (E)-allylic hemiacetal and methoxyacetal showed opposite diastereoselectivity.