(4R,5S)-4-((S)-1-Benzyloxy-3-phenyl-prop-2-ynyl)-5-ethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid amide | 562858-22-4

• 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: (4R,5S)-4-((S)-1-Benzyloxy-3-phenyl-prop-2-ynyl)-5-ethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid amide
• 英文别名: (4R,5S)-5-ethyl-2,2-dimethyl-4-[(1S)-3-phenyl-1-phenylmethoxyprop-2-ynyl]-1,3-dioxolane-4-carboxamide
• CAS: 562858-22-4
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: MKBAUJIDVKJVHO-AWRGLXIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-((S)-1-Benzyloxy-3-phenyl-prop-2-ynyl)-5-ethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid amide 在 potassium permanganate 、 potassium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (4S,5R,9R)-8-Benzoyl-9-benzyloxy-4-ethyl-8-hydroxy-2,2-dimethyl-6-oxo-1,3-dioxa-7-aza-spiro[4.4]nonane-7-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pseurotin A

  摘要：

  [GRAPHICS]The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a gamma-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyidioxirane (DMD).

  DOI：

  10.1021/ol034630s
• 作为产物：
  描述：

  (4R,5S)-4-((S)-1-Benzyloxy-3-phenyl-prop-2-ynyl)-5-ethyl-2,2-dimethyl-[1,3]dioxolane-4-carbonyl chloride 在 氨 作用下， 生成 (4R,5S)-4-((S)-1-Benzyloxy-3-phenyl-prop-2-ynyl)-5-ethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid amide
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pseurotin A

  摘要：

  [GRAPHICS]The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a gamma-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyidioxirane (DMD).

  DOI：

  10.1021/ol034630s

文献信息

• Asymmetric Total Synthesis of (−)-Azaspirene, a Novel Angiogenesis Inhibitor
  作者：Yujiro Hayashi、Mitsuru Shoji、Junichiro Yamaguchi、Kenji Sato、Shinpei Yamaguchi、Takasuke Mukaiyama、Ken Sakai、Yukihiro Asami、Hideaki Kakeya、Hiroyuki Osada

  DOI：10.1021/ja0276826

  日期：2002.10.1

  The asymmetric total synthesis of (-)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2.OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized gamma-lactam moiety without protection of tert-alcohol

  (-)-氮杂紫杉烯（一种血管生成抑制剂）的不对称全合成已经完成，确立了其绝对立体化学。关键步骤是 MgBr2.OEt2 介导的非对映选择性 Mukaiyama 羟醛反应、NaH 促进的炔酰胺分子内环化，以及含有官能化 γ-内酰胺部分的酮的羟醛反应，没有叔醇和酰胺官能团的保护。