2,4-di-O-acetyl-3-O-allyl-5,6-dideoxy-1-O-(4-methoxybenzyl)-1-C-phenyl-hex-5-enitol | 917358-82-8

• 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: 2,4-di-O-acetyl-3-O-allyl-5,6-dideoxy-1-O-(4-methoxybenzyl)-1-C-phenyl-hex-5-enitol
• CAS: 917358-82-8
• 化学式: C₂₇H₃₂O₇
• 分子量: 468.547
• InChiKey: SKZQVIQNQFIHIV-FICKONGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  34.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,4-di-O-acetyl-3-O-allyl-5,6-dideoxy-1-O-(4-methoxybenzyl)-1-C-phenyl-hex-5-enitol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 2,4-di-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-5-enitol
  参考文献：
  名称：

  RCM/PCC oxidation strategy for synthesis of functionalized cyclic α,β-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers

  摘要：

  A novel methodology leading to the synthesis of (+)-triacetoxygoniotriol 2 from D-glucose is described. Construction of the core six-membered alpha, beta-unsaturated lactone moiety involved ring closing metathesis (RCM) followed by a PCC oxidation. Later exploiting the pseudo-symmetry of D-glucose three other diastereomers of triacetoxygoniotriol were synthesized using the developed methodology. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.016
• 作为产物：
  描述：

  1,2-O-(1-methylethylidene)-5-O-(4-methoxybenzyl)-3-O-allyl-5-C-phenyl-5-O-α-D-xylo-furanose 在 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 54.0h， 生成 2,4-di-O-acetyl-3-O-allyl-5,6-dideoxy-1-O-(4-methoxybenzyl)-1-C-phenyl-hex-5-enitol
  参考文献：
  名称：

  RCM/PCC oxidation strategy for synthesis of functionalized cyclic α,β-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers

  摘要：

  A novel methodology leading to the synthesis of (+)-triacetoxygoniotriol 2 from D-glucose is described. Construction of the core six-membered alpha, beta-unsaturated lactone moiety involved ring closing metathesis (RCM) followed by a PCC oxidation. Later exploiting the pseudo-symmetry of D-glucose three other diastereomers of triacetoxygoniotriol were synthesized using the developed methodology. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.016