(5R,6R)-5,6-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-methylhept-3-yn-2-ol | 171863-60-8

• 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: (5R,6R)-5,6-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-methylhept-3-yn-2-ol
• 英文别名: (5R,6R)-7-[tert-butyl(dimethyl)silyl]oxy-2-methyl-5,6-bis(phenylmethoxy)hept-3-yn-2-ol
• CAS: 171863-60-8
• 化学式: C₂₈H₄₀O₄Si
• 分子量: 468.709
• InChiKey: WQOVUGFUDWTDQY-CLJLJLNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,6R)-5,6-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-methylhept-3-yn-2-ol 在 盐酸 、 dicobalt octacarbonyl 、 ammonium cerium(IV) nitrate 、 sodium cyanoborohydride 、 zinc(II) iodide 作用下， 生成 (2R,3R)-2,3-dibenzyloxy-6-methylhept-4-yn-1-ol
  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：

  (2S,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal 在 正丁基锂 、 三乙胺 、 三苯基膦 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 4.67h， 生成 (5R,6R)-5,6-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-methylhept-3-yn-2-ol
  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.