(R)-5-Oxo-tetrahydro-furan-2-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,4,6-tris-benzyloxy-3,5-dihydroxy-cyclohexyl ester | 214282-42-5

• 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: (R)-5-Oxo-tetrahydro-furan-2-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,4,6-tris-benzyloxy-3,5-dihydroxy-cyclohexyl ester
• CAS: 214282-42-5
• 化学式: C₃₂H₃₄O₉
• 分子量: 562.617
• InChiKey: YQZCJUYRZCUZEI-VIXFVTRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  120.75
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  二苯基N,N'-二异丙基亚磷酰胺 、 (R)-5-Oxo-tetrahydro-furan-2-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,4,6-tris-benzyloxy-3,5-dihydroxy-cyclohexyl ester 在 四氮唑 、 间氯过氧苯甲酸 作用下， 生成 (R)-5-Oxo-tetrahydro-furan-2-carboxylic acid (1R,2S,3S,4R,5R,6S)-2,4,6-tris-benzyloxy-3,5-bis-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester
  参考文献：
  名称：

  l-α-Phosphatidyl-d-myo-inositol 3,5-bisphosphate: total synthesis of a new inositol phospholipid via myo-inositol orthoacetate

  摘要：

  The synthesis from myo-inositol of a newly-discovered inositol phospholipid, phosphatidylinositol 3,5-bisphosphate [PtdIns(3,5)P-2], is described. The synthetic strategy, employing inter alia, a trimethylaluminium-mediated regioselective cleavage of a protected inyo-inositol orthoacetate followed by an optical resolution using (R)-(-)-5-oxo-2-tetrahydrofurancarboxylate esters, allows rapid access to dipalmitoyl PtdIns(3,5)P-2. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01422-1
• 作为产物：
  描述：

  tri-O-benzyl-myo-inositol 1,3,5-orthoacetate 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 (R)-5-Oxo-tetrahydro-furan-2-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,4,6-tris-benzyloxy-3,5-dihydroxy-cyclohexyl ester
  参考文献：
  名称：

  l-α-Phosphatidyl-d-myo-inositol 3,5-bisphosphate: total synthesis of a new inositol phospholipid via myo-inositol orthoacetate

  摘要：

  The synthesis from myo-inositol of a newly-discovered inositol phospholipid, phosphatidylinositol 3,5-bisphosphate [PtdIns(3,5)P-2], is described. The synthetic strategy, employing inter alia, a trimethylaluminium-mediated regioselective cleavage of a protected inyo-inositol orthoacetate followed by an optical resolution using (R)-(-)-5-oxo-2-tetrahydrofurancarboxylate esters, allows rapid access to dipalmitoyl PtdIns(3,5)P-2. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01422-1