(2R,3S,4S)-3-N,N-dibenzylamino-4-methyl-2-trimethylsilanyloxy hexanenitrile

• 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: (2R,3S,4S)-3-N,N-dibenzylamino-4-methyl-2-trimethylsilanyloxy hexanenitrile
• 英文别名: (2R,3S,4S)-3-(dibenzylamino)-4-methyl-2-trimethylsilyloxyhexanenitrile
• 化学式: C₂₄H₃₄N₂OSi
• 分子量: 394.632
• InChiKey: AHISWEPILBBIAB-OYDLWJJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 (2S,3S)-2-(N,N-Dibenzylamino)-3-methylpentanal 在 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2R,3S,4S)-3-N,N-dibenzylamino-4-methyl-2-trimethylsilanyloxy hexanenitrile 、 (2S,3S,4S)-3-N,N-dibenzylamino-4-methyl-2-trimethylsilanyloxy hexanenitrile
  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).