(3R,4R)-3,4-dibenzyloxy-1,1-dibromo-5-tert-butyldimethylsilyloxypent-1-ene | 171863-58-4

• 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: (3R,4R)-3,4-dibenzyloxy-1,1-dibromo-5-tert-butyldimethylsilyloxypent-1-ene
• 英文别名: tert-butyl-[(2R,3R)-5,5-dibromo-2,3-bis(phenylmethoxy)pent-4-enoxy]-dimethylsilane
• CAS: 171863-58-4
• 化学式: C₂₅H₃₄Br₂O₃Si
• 分子量: 570.437
• InChiKey: YFGIQOLYHOJCAQ-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.81
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3,4-dibenzyloxy-1,1-dibromo-5-tert-butyldimethylsilyloxypent-1-ene 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.25h， 以96%的产率得到(3R,4R)-3,4-dibenzyloxy-5-tert-butyldimethylsilyloxypent-1-yne
  参考文献：
  名称：

  Highly stereocontrolled total synthesis of (+)-bengamide E

  摘要：

  Diisopropyl D-tartrate 7 was efficiently transformed into the hexacarbonyl dicobalt complexed aldehyde 23. A highly stereocontrolled aldol reaction of 23 with the O,S-acetal 20 in the presence oi tin(IV) chloride provided, after decomplexation, the aldol adduct 21 as the sole product, which was subsequently converted into (+)-bengamide E 5.

  DOI：

  10.1039/p19950002849
• 作为产物：
  描述：

  (2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.42h， 生成 (3R,4R)-3,4-dibenzyloxy-1,1-dibromo-5-tert-butyldimethylsilyloxypent-1-ene
  参考文献：
  名称：

  Highly stereocontrolled total synthesis of (+)-bengamide E

  摘要：

  Diisopropyl D-tartrate 7 was efficiently transformed into the hexacarbonyl dicobalt complexed aldehyde 23. A highly stereocontrolled aldol reaction of 23 with the O,S-acetal 20 in the presence oi tin(IV) chloride provided, after decomplexation, the aldol adduct 21 as the sole product, which was subsequently converted into (+)-bengamide E 5.

  DOI：

  10.1039/p19950002849

文献信息

• Highly stereocontrolled total synthesis of (+)-bengamide E
  作者：Chisato Mukai、Sameh M. Moharram、Osamu Kataoka、Miyoji Hanaoka

  DOI：10.1039/p19950002849

  日期：——

  Diisopropyl D-tartrate 7 was efficiently transformed into the hexacarbonyl dicobalt complexed aldehyde 23. A highly stereocontrolled aldol reaction of 23 with the O,S-acetal 20 in the presence oi tin(IV) chloride provided, after decomplexation, the aldol adduct 21 as the sole product, which was subsequently converted into (+)-bengamide E 5.