tert-butyl-[(3S,4S)-7,7-dibromo-4-methoxy-1-phenylsulfanylhept-6-en-3-yl]oxy-dimethylsilane | 945036-98-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-butyl-[(3S,4S)-7,7-dibromo-4-methoxy-1-phenylsulfanylhept-6-en-3-yl]oxy-dimethylsilane
• CAS: 945036-98-6
• 化学式: C₂₀H₃₂Br₂O₂SSi
• 分子量: 524.432
• InChiKey: ZMYLMIGHLPFJDW-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(3S,4S)-7,7-dibromo-4-methoxy-1-phenylsulfanylhept-6-en-3-yl]oxy-dimethylsilane 在 Pd-BaSO₄ 喹啉 、 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 16.0h， 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-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-phenylsulfanyl-propionaldehyde 在 咪唑 、 4 A molecular sieve 、 三氟化硼乙醚 、 仲丁基锂 、 氯硼烷 、 三苯基膦 、 (+)-B-methoxydiisocamphenylborane 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 tert-butyl-[(3S,4S)-7,7-dibromo-4-methoxy-1-phenylsulfanylhept-6-en-3-yl]oxy-dimethylsilane
  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.