methyl 2-[(2R,3S,4S,5R,6S)-6-[(E,4S,5S)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhept-1-enyl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate | 945037-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl 2-[(2R,3S,4S,5R,6S)-6-[(E,4S,5S)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhept-1-enyl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate
• CAS: 945037-13-8
• 化学式: C₃₆H₇₄O₈Si₃
• 分子量: 719.235
• InChiKey: WWPNLBYAHYGEEI-KZRPUXCASA-N

物化性质

• 沸点：
  625.2±55.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.06
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2R,3S,4S,5R,6S)-6-[(E,4S,5S)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhept-1-enyl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 异丙醇 、 丙酮 为溶剂， 反应 12.0h， 生成 methyl 2-[(2R,3S,4S,5R,6R)-6-[(1S,2R,4S,5S)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-1,2-dihydroxy-4-methoxyheptyl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate 、 methyl 2-[(2R,3S,4S,5R,6R)-6-[(1R,2S,4S,5S)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-1,2-dihydroxy-4-methoxyheptyl]-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：

  3-(叔丁基二甲基硅氧)丙醇 在 Pd-BaSO₄ 2,6-二甲基吡啶 、 喹啉 、 正丁基锂 、 草酰氯 、 三氟化硼乙醚 、 氢气 、 仲丁基锂 、 氯硼烷 、 二甲基亚砜 、 苯硫酚 、 三乙胺 、 三苯基膦 、 (+)-B-methoxydiisocamphenylborane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 16.0h， 生成 methyl 2-[(2R,3S,4S,5R,6S)-6-[(E,4S,5S)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhept-1-enyl]-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.