(S)-2-((2S,4S)-4-Isopropyl-2-methyl-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,3,2]diazaphosphepin-1-yl)-4-methyl-pentanoic acid methyl ester | 494838-68-5

• 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: (S)-2-((2S,4S)-4-Isopropyl-2-methyl-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,3,2]diazaphosphepin-1-yl)-4-methyl-pentanoic acid methyl ester
• 英文别名: methyl (2S)-4-methyl-2-[(2S,7S)-2-methyl-2-oxo-7-propan-2-yl-4,7-dihydro-1H-1,3,2λ5-diazaphosphepin-3-yl]pentanoate
• CAS: 494838-68-5
• 化学式: C₁₅H₂₉N₂O₃P
• 分子量: 316.381
• InChiKey: QZLYRWPNKMEQFX-YPENRWOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-((2S,4S)-4-Isopropyl-2-methyl-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,3,2]diazaphosphepin-1-yl)-4-methyl-pentanoic acid methyl ester 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 以55%的产率得到(S)-2-((2S,4S,5S,6R)-5,6-Dihydroxy-4-isopropyl-2-methyl-2-oxo-2λ⁵-[1,3,2]diazaphosphepan-1-yl)-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  A Concise Route to Structurally Diverse DMP 323 Analogues via Highly Functionalized 1,4-Diamines

  摘要：

  [GRAPHICS]The utility of functionalized 1,4-diamines, produced via a temporary phosphorus tether (P-tether)/ring-closing metathesis (RCM)/hydrolysis sequence, is demonstrated in the synthesis of structurally diverse DMP 323 analogues. These 1,4-diamines are transformed into various seven-membered heterocycles via insertion of the appropriate nuclei "X". Subsequent derivatization generates heterocyclic diols that are similar in structure to DMP 323, a notable member of a class of highly potent inhibitors of HIV protease.

  DOI：

  10.1021/ol027074v
• 作为产物：
  描述：

  methyl (2S)-4-methyl-2-[[methyl-[[(3S)-4-methylpent-1-en-3-yl]amino]phosphoryl]-prop-2-enylamino]pentanoate 在 Ru-based catalyst 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(S)-2-((2S,4S)-4-Isopropyl-2-methyl-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,3,2]diazaphosphepin-1-yl)-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  A Concise Route to Structurally Diverse DMP 323 Analogues via Highly Functionalized 1,4-Diamines

  摘要：

  [GRAPHICS]The utility of functionalized 1,4-diamines, produced via a temporary phosphorus tether (P-tether)/ring-closing metathesis (RCM)/hydrolysis sequence, is demonstrated in the synthesis of structurally diverse DMP 323 analogues. These 1,4-diamines are transformed into various seven-membered heterocycles via insertion of the appropriate nuclei "X". Subsequent derivatization generates heterocyclic diols that are similar in structure to DMP 323, a notable member of a class of highly potent inhibitors of HIV protease.

  DOI：

  10.1021/ol027074v