2,3-dihydroxy-2-(hydroxymethyl)butane-1,4-diyl bis(3,4,5-tris(benzyloxy)benzoate) | 1289559-58-5

• 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: 2,3-dihydroxy-2-(hydroxymethyl)butane-1,4-diyl bis(3,4,5-tris(benzyloxy)benzoate)
• 英文别名: [(2S)-2,3-dihydroxy-3-(hydroxymethyl)-4-[3,4,5-tris(phenylmethoxy)benzoyl]oxybutyl] 3,4,5-tris(phenylmethoxy)benzoate
• CAS: 1289559-58-5
• 化学式: C₆₁H₅₆O₁₃
• 分子量: 997.108
• InChiKey: JHALTSAHVVANHZ-QYAACFOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  74
• 可旋转键数：
  28
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3-dihydroxy-2-(hydroxymethyl)butane-1,4-diyl bis(3,4,5-tris(benzyloxy)benzoate) 、 3,4,5-三苄氧基苯甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以90%的产率得到(+)-(S)-3-hydroxy-3-(((3,4,5-tris(benzyloxy)benzoyl)oxy)methyl)butane-1,2,4-triyl tris(3,4,5-tris(benzyloxy)benzoate)
  参考文献：
  名称：

  Chemoenzymatic total synthesis of potent HIV RNase H inhibitor (−)-1,3,4,5-tetragalloylapiitol

  摘要：

  Starting from racemic dimethyl 2-acetoxy-3-methylenesuccinate, the chemoenzymatic facile total synthesis of (-)-1,3,4,5-tetragalloylapiitol has been demonstrated via an efficient lipase catalyzed resolution followed by a DIBAL reduction-double gallyolation, osmium tetroxide dihydroxylation-double gallyolation, and reductive global O-benzyl deprotection pathway. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.032
• 作为产物：
  描述：

  (R)-2-hydroxy-3-methylenesuccinic acid dimethyl ester 在 咪唑 、 4-二甲氨基吡啶 、 四氧化锇 、 四丁基氟化铵 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 叔丁醇 为溶剂， 反应 17.33h， 生成 2,3-dihydroxy-2-(hydroxymethyl)butane-1,4-diyl bis(3,4,5-tris(benzyloxy)benzoate)
  参考文献：
  名称：

  Chemoenzymatic total synthesis of potent HIV RNase H inhibitor (−)-1,3,4,5-tetragalloylapiitol

  摘要：

  Starting from racemic dimethyl 2-acetoxy-3-methylenesuccinate, the chemoenzymatic facile total synthesis of (-)-1,3,4,5-tetragalloylapiitol has been demonstrated via an efficient lipase catalyzed resolution followed by a DIBAL reduction-double gallyolation, osmium tetroxide dihydroxylation-double gallyolation, and reductive global O-benzyl deprotection pathway. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.032

文献信息

• Chemoenzymatic total synthesis of potent HIV RNase H inhibitor (−)-1,3,4,5-tetragalloylapiitol
  作者：Ramesh U. Batwal、Ramesh M. Patel、Narshinha P. Argade

  DOI：10.1016/j.tetasy.2010.11.032

  日期：2011.1

  Starting from racemic dimethyl 2-acetoxy-3-methylenesuccinate, the chemoenzymatic facile total synthesis of (-)-1,3,4,5-tetragalloylapiitol has been demonstrated via an efficient lipase catalyzed resolution followed by a DIBAL reduction-double gallyolation, osmium tetroxide dihydroxylation-double gallyolation, and reductive global O-benzyl deprotection pathway. (C) 2010 Elsevier Ltd. All rights reserved.