O-(4aR,5aS,9aR,10R,10aS)-octahydro-4a-methoxy-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran-10-yl S-methyl carbonodithioate | 916499-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(4aR,5aS,9aR,10R,10aS)-octahydro-4a-methoxy-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran-10-yl S-methyl carbonodithioate
• 英文别名: O-[(1R,3S,8R,9R,10S)-1-methoxy-2-oxa-6,12-dithiatricyclo[8.4.0.03,8]tetradecan-9-yl] methylsulfanylmethanethioate
• CAS: 916499-23-5
• 化学式: C₁₄H₂₂O₃S₄
• 分子量: 366.591
• InChiKey: PZOSAYDSIVIXGV-OIRVYTLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O-(4aR,5aS,9aR,10R,10aS)-octahydro-4a-methoxy-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran-10-yl S-methyl carbonodithioate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以91%的产率得到(4aR,5aS,9aS,10aS)-octahydro-4a-methoxy-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran
  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：

  (αR,6S)-α-[(3R,4S)-tetrahydro-4-hydroxy-2H-thiopyran-3-yl]-1,4-dioxa-8-thiaspiro[4.5]decane-6-methanol 在 咪唑 、 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 O-(4aR,5aS,9aR,10R,10aS)-octahydro-4a-methoxy-1H,3H,5aH-dithiopyrano[4,3-b:3',4'-e]pyran-10-yl S-methyl carbonodithioate
  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.