(4R,5S,6R)-4-methoxy-5-(4-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one | 947305-41-1

• 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: (4R,5S,6R)-4-methoxy-5-(4-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one
• 英文别名: (4R,5S,6R)-6-ethenyl-4-methoxy-5-[(4-methoxyphenyl)methoxy]oxan-2-one
• CAS: 947305-41-1
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: MEMAALVVMXKPNR-IIAWOOMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 (4R,5S,6R)-4-methoxy-5-(4-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one 在 sodium methylate 作用下， 反应 3.0h， 以83%的产率得到methyl (3R,4R,5R)-5-hydroxy-3-methoxy-4-(4-methoxybenzyloxy)hept-6-enoate
  参考文献：
  名称：

  Synthesis of sporiolide B from d-glucal

  摘要：

  A total synthesis of the 12-membered ring natural macrolide, sporiolide B, was achieved from D-glucal in 17 steps with 4.8% overall yield. The required stereochemical configuration at C-3 and C-5 in sporiolide B was easily introduced by applying a Mitsunobu reaction on the chiral template D-glucal. Yamaguchi esterification and ring closing metathesis greatly improved the access to the target compound. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.013
• 作为产物：
  描述：

  (2R,3S,4R)-4-methoxy-3-(4-methoxybenzyloxy)-2-vinyl-3,4-dihydro-2H-pyran 在 silica gel 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以70%的产率得到(4R,5S,6R)-4-methoxy-5-(4-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one
  参考文献：
  名称：

  Synthesis of sporiolide B from d-glucal

  摘要：

  A total synthesis of the 12-membered ring natural macrolide, sporiolide B, was achieved from D-glucal in 17 steps with 4.8% overall yield. The required stereochemical configuration at C-3 and C-5 in sporiolide B was easily introduced by applying a Mitsunobu reaction on the chiral template D-glucal. Yamaguchi esterification and ring closing metathesis greatly improved the access to the target compound. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.013