(αR,6S)-α-[(3S,4S)-4-triethylsilyloxytetrahydro-2H-thiopyran-3-yl]-1,4-dioxa-8-thiaspiro[4.5]decane-6-methanol | 916499-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (αR,6S)-α-[(3S,4S)-4-triethylsilyloxytetrahydro-2H-thiopyran-3-yl]-1,4-dioxa-8-thiaspiro[4.5]decane-6-methanol
• 英文别名: (R)-[(6S)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl]-[(3S,4S)-4-triethylsilyloxythian-3-yl]methanol
• CAS: 916499-18-8
• 化学式: C₁₉H₃₆O₄S₂Si
• 分子量: 420.71
• InChiKey: PQNJVMRAZCHZOD-VSZNYVQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (αR,6S)-α-[(3S,4S)-4-triethylsilyloxytetrahydro-2H-thiopyran-3-yl]-1,4-dioxa-8-thiaspiro[4.5]decane-6-methanol 在 咪唑 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 Raney nickel W-2 、 三正丁基氢锡 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.42h， 生成 2H-1,3,5-噁二嗪,四氢-3,5-二(1-甲基乙基)-
  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：

  四氢噻喃-4-酮 在 2,6-二甲基吡啶 、 水 、 L-Selectride 、 (S)-5-(吡咯烷-2-基)-1H-四唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 195.17h， 生成 (αR,6S)-α-[(3S,4S)-4-triethylsilyloxytetrahydro-2H-thiopyran-3-yl]-1,4-dioxa-8-thiaspiro[4.5]decane-6-methanol
  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.