(2R,3R,4aR,6S,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3,6-trimethyl-6,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-5-one | 1192589-69-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,3R,4aR,6S,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3,6-trimethyl-6,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-5-one
• CAS: 1192589-69-7
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: UPWUHKVHAKFLKY-AUINJBQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4aR,6S,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3,6-trimethyl-6,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-5-one 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到环己酮,2,3,4-三羟基-6-甲基-,(2R,3S,4S,6S)-
  参考文献：
  名称：

  Carbocyclization of Carbohydrates: Diastereoselective Synthesis of (+)-Gabosine F, (−)-Gabosine O, and (+)-4-epi-Gabosine O

  摘要：

  Exploitation of silica gel/chloramine T mediated intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar-derived oximes to carbocycles furnished the first synthesis of gabosine F from L-arabinose in 12 steps with 23% overall yield, thereby confirming it absolute configuration. Similarly, efficient syntheses of gabosine O and 4-epi-gabosine O were accomplished from D-Mannose in 9 and 11 steps with 41% and 38% overall yields, respectively, involving INOC, regioselective dehydration, and diastereciselective hydrogenation as the key steps.

  DOI：

  10.1021/ol902071e
• 作为产物：
  描述：

  (2R,3R,4aR,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-6-methylidene-4a,7,8,8a-tetrahydrobenzo[b][1,4]dioxin-5-one 在 氢气 、 镍 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 1.0h， 以37 mg的产率得到(2R,3R,4aR,6S,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3,6-trimethyl-6,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-5-one
  参考文献：
  名称：

  Carbocyclization of Carbohydrates: Diastereoselective Synthesis of (+)-Gabosine F, (−)-Gabosine O, and (+)-4-epi-Gabosine O

  摘要：

  Exploitation of silica gel/chloramine T mediated intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar-derived oximes to carbocycles furnished the first synthesis of gabosine F from L-arabinose in 12 steps with 23% overall yield, thereby confirming it absolute configuration. Similarly, efficient syntheses of gabosine O and 4-epi-gabosine O were accomplished from D-Mannose in 9 and 11 steps with 41% and 38% overall yields, respectively, involving INOC, regioselective dehydration, and diastereciselective hydrogenation as the key steps.

  DOI：

  10.1021/ol902071e