(2S,3R,4S)-N²,N²-dibenzyl-N³-(4-methoxyphenyl)-1,5-diphenyl-2,3,4-pentanetriamine | 501668-75-3

• 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,3R,4S)-N²,N²-dibenzyl-N³-(4-methoxyphenyl)-1,5-diphenyl-2,3,4-pentanetriamine
• 英文别名: (2S,3R,4S)-4-N,4-N-dibenzyl-3-N-(4-methoxyphenyl)-1,5-diphenylpentane-2,3,4-triamine
• CAS: 501668-75-3
• 化学式: C₃₈H₄₁N₃O
• 分子量: 555.763
• InChiKey: ZEMPAQJAONFGQO-XEZIGOATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  50.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-N²,N²-dibenzyl-N³-(4-methoxyphenyl)-1,5-diphenyl-2,3,4-pentanetriamine 在 10percent Pd/C 甲酸铵 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 生成 (2S,4S)-N³-(4-methoxyphenyl)-1,5-diphenyl-N²,N²-di-(p-toluenesulfonyl)-2,3,4-pentanetriamine
  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：

  (2S,3S)-N²,N²-Dibenzyl-N³-(4-methoxy-phenyl)-4-nitro-1,5-diphenyl-pentane-2,3-diamine 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (2S,3R,4R)-N²,N²-dibenzyl-N³-(4-methoxyphenyl)-1,5-diphenyl-2,3,4-pentanetriamine 、 (2S,3R,4S)-N²,N²-dibenzyl-N³-(4-methoxyphenyl)-1,5-diphenyl-2,3,4-pentanetriamine
  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).