(4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester | 137649-68-4

• 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: (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester
• 英文别名: (4S,5R,6R,7S)-4,7-Bis-2,9-dimethyl-5,6-decanediol；1,4-bis<(N-Cbz)amino>-1,4-diisobutyl-2,3-diol；(4S,5R,6R,7S)-4,7-Bis[N-(benzyloxycarbonyl)amino]-2,9-dimethyl-5,6-decanediol；benzyl N-[(4S,5R,6R,7S)-5,6-dihydroxy-2,9-dimethyl-7-(phenylmethoxycarbonylamino)decan-4-yl]carbamate
• CAS: 137649-68-4
• 化学式: C₂₈H₄₀N₂O₆
• 分子量: 500.635
• InChiKey: NIKQMZQRGOLNQZ-QEGGNFSNSA-N

物化性质

• 沸点：
  683.0±55.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 45.5h， 生成 benzyl N-[(2S)-1-[[(2S)-1-[[(1S)-1-[(4R,5R)-2,2-dimethyl-5-[(1S)-3-methyl-1-[[(2S)-3-methyl-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoyl]amino]butyl]-1,3-dioxolan-4-yl]-3-methylbutyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Development of a New Type of Protease Inhibitors, Efficacious against FIV and HIV Variants

  摘要：

  Based on the structural analysis of FIV protease and drug-resistant HIV proteases and molecular modeling, a new type of inhibitors with a small P3 residue has been developed. These inhibitors are effective against HIV and its drug-resistant mutants, as well as SIV and FIV. Modification of existing HIV protease inhibitors by reducing the size of the P3 residue has the same effect. This finding provides a new strategy for the development of HIV protease inhibitors effective against the wild-type and drug-resistant mutants. It further supports the use of FIV protease as a useful model for drug-resistant HIV proteases, which often have a more constricted binding region for the P3 group or the combined P3 and P1 groups.

  DOI：

  10.1021/ja982893p
• 作为产物：
  描述：

  N-carbobenzoxy-L-leucinal 在 vanadium(III) chloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以15%的产率得到(4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Expedient solid-phase synthesis of both symmetric and asymmetric diol libraries targeting aspartic proteases

  摘要：

  C-2-symmetric diols have been shown to be highly potent against HIV-1 protease (PR). However, gaining access to these compounds has been hampered by the need of multistep solution-phase reactions which are often tedious and inefficient. In this Letter, we have disclosed a solid-phase strategy for rapid preparation of small molecule-based, symmetric and asymmetric diols as potential HIV-1 protease inhibitors. Upon biological screening, we found one of them, SYM-5, to be a potent and selective inhibitor (K-i = 400 nM) against HIV-1 protease. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.041

文献信息

• Pinacol homocoupling of (S)-2-[N-(benzyloxycarbonyl)amino] aldehydes by [V2Cl3(THF)6]2[Zn2Cl6]. Synthesis of C2-symmetric (1S,2R,3R,4S)-1,4-diamino 2,3-diols
  作者：Andrei W. Konradi、Steven F. Pedersen

  DOI：10.1021/jo00027a009

  日期：1992.1

  Six (S)-2-[N-(benzyloxycarbonyl)amino] aldehydes 3a-f were homocoupled by [V2Cl3(THF)6]2[Zn2Cl6] (1) to give C2-symmetric (1S,2R,3R,4S)-1,4-bis[N-(benzyloxycarbonyl)amino] 2,3-diols 4a-f in good yield. High-yield conversions of the diols to bisoxazolidinones (sodium hydride, tetrahydrofuran) and to the deprotected (1S,2R,3R,4S)-1,4-diamino 2,3-diol dihydrochloride salts (10% Pd/C, formic acid, HCl in ether) were performed.