(4aR,5aS,9aS,10R,10aS)-octahydro-4a-methoxy-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran-10-ol | 916499-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,5aS,9aS,10R,10aS)-octahydro-4a-methoxy-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran-10-ol
• 英文别名: (1R,3S,8S,9R,10S)-1-methoxy-2-oxa-6,12-dithiatricyclo[8.4.0.03,8]tetradecan-9-ol
• CAS: 916499-20-2
• 化学式: C₁₂H₂₀O₃S₂
• 分子量: 276.421
• InChiKey: BGTPFMLSMXJKHR-YBXAARCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aR,5aS,9aS,10R,10aS)-octahydro-4a-methoxy-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran-10-ol 在 咪唑 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 6.5h， 生成 (4aR,5aS,9aS,10aS)-octahydro-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran-4a-ol
  参考文献：
  名称：

  Thiopyran Route to Polypropionates:  An Efficient Synthesis of Serricornin

  摘要：

  The synthesis of serricornin [(4S, 6S, 7S)-7-hydroxy-4,6-dimethylnonan- 3-one], a sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.), in seven steps from readily available racemic 1,4-dioxa-8- thiaspiro-[4.5] decane-6-carboxaldehyde (6) is described. The key steps include enantioselective aldol reaction of 6 with tetrahydrothiopyran-4- one catalyzed by 5-[(2S)-pyrrolidine-2-yl]-1H- tetrazole to fabricate the tetrapropionate skeleton, stereoselective (LiBu3BH)-Bu-s reduction of the resulting aldol adduct, Barton-McCombie deoxygenation, and Raney nickel desulfurization.

  DOI：

  10.1021/jo061747w
• 作为产物：
  描述：

  (-)-(3S)-3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(triethylsilyloxy)methyl]tetrahydro-4H-thiopyran-4-one 在 盐酸 、 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (4aR,5aS,9aS,10R,10aS)-octahydro-4a-methoxy-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran-10-ol
  参考文献：
  名称：

  Thiopyran Route to Polypropionates:  An Efficient Synthesis of Serricornin

  摘要：

  The synthesis of serricornin [(4S, 6S, 7S)-7-hydroxy-4,6-dimethylnonan- 3-one], a sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.), in seven steps from readily available racemic 1,4-dioxa-8- thiaspiro-[4.5] decane-6-carboxaldehyde (6) is described. The key steps include enantioselective aldol reaction of 6 with tetrahydrothiopyran-4- one catalyzed by 5-[(2S)-pyrrolidine-2-yl]-1H- tetrazole to fabricate the tetrapropionate skeleton, stereoselective (LiBu3BH)-Bu-s reduction of the resulting aldol adduct, Barton-McCombie deoxygenation, and Raney nickel desulfurization.

  DOI：

  10.1021/jo061747w

文献信息

• Thiopyran Route to Polypropionates:  An Efficient Synthesis of Serricornin
  作者：Dale E. Ward、Vishal Jheengut、Garrison E. Beye

  DOI：10.1021/jo061747w

  日期：2006.11.1

  The synthesis of serricornin [(4S, 6S, 7S)-7-hydroxy-4,6-dimethylnonan- 3-one], a sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.), in seven steps from readily available racemic 1,4-dioxa-8- thiaspiro-[4.5] decane-6-carboxaldehyde (6) is described. The key steps include enantioselective aldol reaction of 6 with tetrahydrothiopyran-4- one catalyzed by 5-[(2S)-pyrrolidine-2-yl]-1H- tetrazole to fabricate the tetrapropionate skeleton, stereoselective (LiBu3BH)-Bu-s reduction of the resulting aldol adduct, Barton-McCombie deoxygenation, and Raney nickel desulfurization.