(2S,3R,4R,5S)-2,5-Bis-1,6-di(3-indolyl)-3,4-hexanediol | 137649-72-0

• 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,4R,5S)-2,5-Bis-1,6-di(3-indolyl)-3,4-hexanediol
• 英文别名: (2,5-Bis[[(benzyloxy)carbonyl]amino]-1,2,5,6-tetradeoxy-1,6-di-1h-indol-3-yl-l-iditol)；benzyl N-[(2S,3R,4R,5S)-3,4-dihydroxy-1,6-bis(1H-indol-3-yl)-5-(phenylmethoxycarbonylamino)hexan-2-yl]carbamate
• CAS: 137649-72-0
• 化学式: C₃₈H₃₈N₄O₆
• 分子量: 646.743
• InChiKey: PEFHEMBSLIFFRC-CLLHQPRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S)-2,5-Bis-1,6-di(3-indolyl)-3,4-hexanediol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (4S,5R)-4-(1H-indol-3-ylmethyl)-5-[(4S,5R)-4-(1H-indol-3-ylmethyl)-2-oxo-1,3-oxazolidin-5-yl]-1,3-oxazolidin-2-one 、 苯甲醇
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00027a009
• 作为产物：
  描述：

  benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate 在 盐酸 、 pyridine-SO3 complex 、 2 、 二甲基亚砜 、 三乙胺 作用下， 反应 16.0h， 生成 (2S,3R,4R,5S)-2,5-Bis-1,6-di(3-indolyl)-3,4-hexanediol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00027a009

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.