(2S)-2-(dibenzylamino)-4-nitro-1,5-diphenylpentan-3-ol | 501668-70-8

• 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: (2S)-2-(dibenzylamino)-4-nitro-1,5-diphenylpentan-3-ol
• CAS: 501668-70-8
• 化学式: C₃₁H₃₂N₂O₃
• 分子量: 480.607
• InChiKey: BAWIPAKTTMKKFR-LRBNCQHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-(dibenzylamino)-4-nitro-1,5-diphenylpentan-3-ol 在 10percent Pd/C sodium tetrahydroborate 、 甲酸铵 、 sodium carbonate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 异丙醇 为溶剂， 反应 6.66h， 生成 (2S,4S)-1,5-diphenyl-2,4-[di-(p-toluenesulfonylamino)] pentan-3-ol
  参考文献：
  名称：

  Concise and Stereocontrolled Synthesis of Pseudo-C₂-symmetric Diamino Alcohols and Triamines for Use in HIV Protease Inhibitors

  摘要：

  A new protocol is described for the stereocontrolled synthesis of pseudo-C-2-symmetric core units of interest as candidates for HIV protease inhibition. Addition of unbranched and branched organolithium reagents to cyanohydrins from L-phenylalaninal and L-isoleucinal, followed by in situ reduction of the intermediate imines and CHT deprotection under MW irradiation, led to 1,3-diamino alcohols 6a and 8a as the major products in satisfactory to good yields. The first preparation of a previously unreported pseudo-C-2-symmetric triamino derivative was accomplished expeditiously via high-yielding nitro-Mannich addition of the silylnitronate, from 2-phenyl-1-nitroethane, to the PMP imine derived from L-phenylalaninal. Reduction of the nitro group in the moderately unstable nitro diamine adduct, followed by chromatographic separation of the required diastereoisomer and CHT debenzylation under MW irradiation, led to the 2-PMP-protected triamine 19 isolated as a bis(sulfonamide).

  DOI：

  10.1021/jo026616j
• 作为产物：
  描述：

  Β-硝基苯乙烷 、 苯丙醛,a-[二(苯基甲基)氨基]-,(S)- 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以87%的产率得到(2S)-2-(dibenzylamino)-4-nitro-1,5-diphenylpentan-3-ol
  参考文献：
  名称：

  Concise and Stereocontrolled Synthesis of Pseudo-C₂-symmetric Diamino Alcohols and Triamines for Use in HIV Protease Inhibitors

  摘要：

  A new protocol is described for the stereocontrolled synthesis of pseudo-C-2-symmetric core units of interest as candidates for HIV protease inhibition. Addition of unbranched and branched organolithium reagents to cyanohydrins from L-phenylalaninal and L-isoleucinal, followed by in situ reduction of the intermediate imines and CHT deprotection under MW irradiation, led to 1,3-diamino alcohols 6a and 8a as the major products in satisfactory to good yields. The first preparation of a previously unreported pseudo-C-2-symmetric triamino derivative was accomplished expeditiously via high-yielding nitro-Mannich addition of the silylnitronate, from 2-phenyl-1-nitroethane, to the PMP imine derived from L-phenylalaninal. Reduction of the nitro group in the moderately unstable nitro diamine adduct, followed by chromatographic separation of the required diastereoisomer and CHT debenzylation under MW irradiation, led to the 2-PMP-protected triamine 19 isolated as a bis(sulfonamide).

  DOI：

  10.1021/jo026616j

文献信息

• Concise and Stereocontrolled Synthesis of Pseudo-<i>C</i>₂-symmetric Diamino Alcohols and Triamines for Use in HIV Protease Inhibitors
  作者：Luca Bernardi、Bianca F. Bonini、Gabriella Dessole、Mariafrancesca Fochi、Mauro Comes-Franchini、Silvia Gavioli、Alfredo Ricci、Greta Varchi

  DOI：10.1021/jo026616j

  日期：2003.2.1

  A new protocol is described for the stereocontrolled synthesis of pseudo-C-2-symmetric core units of interest as candidates for HIV protease inhibition. Addition of unbranched and branched organolithium reagents to cyanohydrins from L-phenylalaninal and L-isoleucinal, followed by in situ reduction of the intermediate imines and CHT deprotection under MW irradiation, led to 1,3-diamino alcohols 6a and 8a as the major products in satisfactory to good yields. The first preparation of a previously unreported pseudo-C-2-symmetric triamino derivative was accomplished expeditiously via high-yielding nitro-Mannich addition of the silylnitronate, from 2-phenyl-1-nitroethane, to the PMP imine derived from L-phenylalaninal. Reduction of the nitro group in the moderately unstable nitro diamine adduct, followed by chromatographic separation of the required diastereoisomer and CHT debenzylation under MW irradiation, led to the 2-PMP-protected triamine 19 isolated as a bis(sulfonamide).