(2R,3S,4R,5R)-4,5-dibenzyloxy-3-hydroxy-2-methoxy-8-methyl-N-<(3S)-2-oxoazepan-3-yl>non-6-ynamide | 171863-69-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S,4R,5R)-4,5-dibenzyloxy-3-hydroxy-2-methoxy-8-methyl-N-<(3S)-2-oxoazepan-3-yl>non-6-ynamide
• 英文别名: (2R,3R,4R,5R)-3-hydroxy-2-methoxy-8-methyl-N-[(3S)-2-oxoazepan-3-yl]-4,5-bis(phenylmethoxy)non-6-ynamide
• CAS: 171863-69-7
• 化学式: C₃₁H₄₀N₂O₆
• 分子量: 536.668
• InChiKey: COZSSVATGNBEQF-MLZSXWJDSA-N

物化性质

• 沸点：
  775.6±60.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-4,5-dibenzyloxy-3-hydroxy-2-methoxy-8-methyl-N-<(3S)-2-oxoazepan-3-yl>non-6-ynamide 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以65%的产率得到(E,2R,3R,4S,5R)-3,4,5-三羟基-2-甲氧基-8-甲基-N-[(3S)-2-氧代氮杂环庚-3-基]壬-6-烯酰胺
  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：

  S-tert-butyl (2R,3S,4R,5R)-4,5-dibenzyloxy-3-hydroxy-2-methoxy-8-methylnon-6-ynethioate 在 三甲基铝 、 silver trifluoroacetate 作用下， 以 甲醇 为溶剂， 反应 10.25h， 生成 (2R,3S,4R,5R)-4,5-dibenzyloxy-3-hydroxy-2-methoxy-8-methyl-N-<(3S)-2-oxoazepan-3-yl>non-6-ynamide
  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.