(2S,3S)-5-methyl-3-phthalimidohexane-1,2-diol | 207281-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (2S,3S)-5-methyl-3-phthalimidohexane-1,2-diol
• 英文别名: 2-[(2S,3S)-1,2-dihydroxy-5-methylhexan-3-yl]isoindole-1,3-dione
• CAS: 207281-69-4
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: AZBKYAOWMDWPOT-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-5-methyl-3-phthalimidohexane-1,2-diol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 38.0h， 以69%的产率得到(S)-((S)-3-methyl-1-phthalimidobutyl)oxirane
  参考文献：
  名称：

  A General, Catalytic, and Enantioselective Synthesis of (S)-γ-[(S)-1-Aminoalkyl]-γ-lactones

  摘要：

  A catalytic asymmetric synthesis of N-phthaloyl (S)-gamma-[(S)-1-aminoalkyl]-gamma-lactones, widely used intermediates in the preparation of hydroxyethylene dipeptide isosteres, is described. The highly enantiopure epoxy alcohols arising from the Sharpless epoxidation of (E)-allyl alcohols are first converted to (S)-N-phthaloyl-[(S)-1-aminoalkyl]oxiranes by means of an efficient four-step sequence involving the regio- and stereoselective ring opening of the starting epoxide by azide, reduction, phthaloylation, and intramolecular Mitsunobu cyclization of the intermediate phthalimido diol. Treatment of the resulting oxirane with lithium (1R)-menthyloxyacetylide in the presence of boron trifluoride etherate, followed by in situ hydrolysis of the ynol ether, leads to a (4R, 5S)-5-phthalimido-4-hydroxy ester. A Mitsunobu reaction with p-nitrobenzoic acid (which establishes the correct (S)configuration at C-4) and subsequent selective saponification of the benzoate and cyclization of the inverted hydroxy ester afford the target N-protected (S)-gamma-[(S)-1-aminoalkyl]-gamma-lactones. Using this methodology, lactones 19 and 26 were obtained in seven steps from the readily available epoxy alcohols 5 and 20, respectively, in high enantiomeric purity.

  DOI：

  10.1021/jo9720851
• 作为产物：
  描述：

  (2R,3R)-2,3-epoxy-5-methyl-1-hexanol 在 palladium on activated charcoal Ti(N3)2(OiPr)2 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 苯 为溶剂， 25.0~85.0 ℃ 、101.33 kPa 条件下， 反应 33.25h， 生成 (2S,3S)-5-methyl-3-phthalimidohexane-1,2-diol
  参考文献：
  名称：

  A General, Catalytic, and Enantioselective Synthesis of (S)-γ-[(S)-1-Aminoalkyl]-γ-lactones

  摘要：

  A catalytic asymmetric synthesis of N-phthaloyl (S)-gamma-[(S)-1-aminoalkyl]-gamma-lactones, widely used intermediates in the preparation of hydroxyethylene dipeptide isosteres, is described. The highly enantiopure epoxy alcohols arising from the Sharpless epoxidation of (E)-allyl alcohols are first converted to (S)-N-phthaloyl-[(S)-1-aminoalkyl]oxiranes by means of an efficient four-step sequence involving the regio- and stereoselective ring opening of the starting epoxide by azide, reduction, phthaloylation, and intramolecular Mitsunobu cyclization of the intermediate phthalimido diol. Treatment of the resulting oxirane with lithium (1R)-menthyloxyacetylide in the presence of boron trifluoride etherate, followed by in situ hydrolysis of the ynol ether, leads to a (4R, 5S)-5-phthalimido-4-hydroxy ester. A Mitsunobu reaction with p-nitrobenzoic acid (which establishes the correct (S)configuration at C-4) and subsequent selective saponification of the benzoate and cyclization of the inverted hydroxy ester afford the target N-protected (S)-gamma-[(S)-1-aminoalkyl]-gamma-lactones. Using this methodology, lactones 19 and 26 were obtained in seven steps from the readily available epoxy alcohols 5 and 20, respectively, in high enantiomeric purity.

  DOI：

  10.1021/jo9720851