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-methoxy-3,5-dimethyloxan-2-yl]acetate | 945037-06-9

• 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,6S)-6-[(Z,4S,5S)-7-(benzenesulfonyl)-5-[tert-butyl(dimethyl)silyl]oxy-4-methoxyhept-1-enyl]-4-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-3,5-dimethyloxan-2-yl]acetate
• CAS: 945037-06-9
• 化学式: C₃₇H₆₆O₉SSi₂
• 分子量: 743.163
• InChiKey: AUFVHKGTLJWXNU-HLNKTHQISA-N

物化性质

• 沸点：
  692.5±55.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.17
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  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-methoxy-3,5-dimethyloxan-2-yl]acetate 在 四氧化锇 、 四甲基乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 methyl 2-[(2R,3S,4S,5R,6R)-6-[(1S,2S,4S,5S)-7-(benzenesulfonyl)-5-[tert-butyl(dimethyl)silyl]oxy-1,2-dihydroxy-4-methoxyheptyl]-4-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-3,5-dimethyloxan-2-yl]acetate 、 methyl 2-[(2R,3S,4S,5R,6R)-6-[(1R,2R,4S,5S)-7-(benzenesulfonyl)-5-[tert-butyl(dimethyl)silyl]oxy-1,2-dihydroxy-4-methoxyheptyl]-4-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-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：

  (3S,4S)-4-((tert-butyldimethylsilyl)oxy)-3-methoxy-6-(phenylthio)hexanal 在 Pd-BaSO₄ 喹啉 、 正丁基锂 、 4 A molecular sieve 、 氢气 、 4-甲基苯磺酸吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 27.0h， 生成 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-methoxy-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.