[(2R,3R,4aR,6R,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-5-oxo-6,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-6-yl]methyl acetate | 1192589-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4aR,6R,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-5-oxo-6,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-6-yl]methyl acetate
• CAS: 1192589-68-6
• 化学式: C₁₅H₂₄O₈
• 分子量: 332.351
• InChiKey: GIXCSTLPGGVIMX-JXKDEVGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4aR,6R,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-5-oxo-6,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-6-yl]methyl acetate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 (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
  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,6R,8S,8aS)-8-hydroxy-6-(hydroxymethyl)-2,3-dimethoxy-2,3-dimethyl-6,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-5-one 、 乙酰氯 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以87%的产率得到[(2R,3R,4aR,6R,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-5-oxo-6,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-6-yl]methyl acetate
  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