(αR,6S)-α-[(3R,4S)-tetrahydro-4-hydroxy-2H-thiopyran-3-yl]-1,4-dioxa-8-thiaspiro[4.5]decane-6-methanol | 916499-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (αR,6S)-α-[(3R,4S)-tetrahydro-4-hydroxy-2H-thiopyran-3-yl]-1,4-dioxa-8-thiaspiro[4.5]decane-6-methanol
• 英文别名: (3R,4S)-3-[(R)-[(6S)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl]-hydroxymethyl]thian-4-ol
• CAS: 916499-17-7
• 化学式: C₁₃H₂₂O₄S₂
• 分子量: 306.447
• InChiKey: DTXMAZCECSOBMI-NOOOWODRSA-N

物化性质

• 沸点：
  516.0±50.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 、 2,6-二甲基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.67h， 生成 O-(R)-[(6S)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl][(3S,4S)-4-(triethylsilyloxy)tetrahydro-2H-thiopyran-3-yl]methyl 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
• 作为产物：
  描述：

  1,4-dioxa-8-thiaspiro<4.5>decane-6-carboxaldehyde 在 水 、 L-Selectride 、 (S)-5-(吡咯烷-2-基)-1H-四唑 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 195.0h， 生成 (αR,6S)-α-[(3R,4S)-tetrahydro-4-hydroxy-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.