(3R,4R)-3-methoxy-4-[(1S,2R)-5-methyl-1,2-bis(phenylmethoxy)hex-3-ynyl]oxetan-2-one | 171863-68-6

• 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-methoxy-4-[(1S,2R)-5-methyl-1,2-bis(phenylmethoxy)hex-3-ynyl]oxetan-2-one
• CAS: 171863-68-6
• 化学式: C₂₅H₂₈O₅
• 分子量: 408.494
• InChiKey: JYBDPEZNPFGPSA-UEQSERJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-methoxy-4-[(1S,2R)-5-methyl-1,2-bis(phenylmethoxy)hex-3-ynyl]oxetan-2-one 在 氨 、 三甲基铝 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 5.75h， 生成 (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 silver trifluoroacetate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (3R,4R)-3-methoxy-4-[(1S,2R)-5-methyl-1,2-bis(phenylmethoxy)hex-3-ynyl]oxetan-2-one
  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.