2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol | 844866-74-6

• 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: 2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol
• 英文别名: [(3R,4S,5S,6R)-5,6-diacetyloxy-6-phenyl-4-prop-2-enoxyhex-1-en-3-yl] acetate
• CAS: 844866-74-6
• 化学式: C₂₁H₂₆O₇
• 分子量: 390.433
• InChiKey: SCHIWCKAGIZDPC-CGXNFDGLSA-N

物化性质

• 沸点：
  462.1±45.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到1,2,4-tri-O-acetyl-3,7-anhydro-5,6-dideoxy-1-C-phenyl-hept-5-enitol
  参考文献：
  名称：

  Enantiospecific synthesis of [7R,6S,5S,4R]-triacetoxy-(−)-goniotriol

  摘要：

  A short and efficient synthesis of [7R,6S,5S,4R]-triacetoxy-(-)-goniotriol starting form D-glucose is described. A sequence of ring closing metathesis (RCM) followed by a PCC oxidation was used to construct the core six-membered alpha,beta-unsaturated lactone moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01048-1
• 作为产物：
  描述：

  3-O-allyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 在 4-二甲氨基吡啶 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 68.0h， 生成 2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-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