2-((2R,4aR,6S,7R,8aS)-2-phenyl-7-((E)-2-(phenylsulfonyl)vinyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)acetaldehyde | 1246760-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((2R,4aR,6S,7R,8aS)-2-phenyl-7-((E)-2-(phenylsulfonyl)vinyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)acetaldehyde
• 英文别名: 2-[(2R,4aR,6S,7R,8aS)-7-[(E)-2-(benzenesulfonyl)ethenoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]acetaldehyde
• CAS: 1246760-19-9
• 化学式: C₂₃H₂₄O₇S
• 分子量: 444.505
• InChiKey: VKCQJPIHRKYQAM-JILQDHGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((2R,4aR,6S,7R,8aS)-2-phenyl-7-((E)-2-(phenylsulfonyl)vinyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)acetaldehyde 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到(2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal
  参考文献：
  名称：

  SmI2-induced cyclization of (E)- and (Z)-β-alkoxyvinyl sulfones with aldehydes

  摘要：

  SmI2-induced reaction of (E)- and (Z)-beta-alkoxyvinyl sulfones onto an aldehyde function afforded 2,6-syn-2,3-trans- and 2,6-syn-2,3-cis-tetrahydropyran-3-ols, respectively, via stereoselective cyclization. This reaction was applied to the synthesis of 2-methyl-tetrahydropyran, corresponding to the N-ring of gymnocin-A, and 2-exo-methylene-tetrahydropyran, a key intermediate for convergent synthesis of polycyclic ethers based on the Suzuki-Miyaura reaction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.066
• 作为产物：
  描述：

  ethyl 2-[(2R,4aR,6S,7R,8aS)-7-[(E)-2-(benzenesulfonyl)ethenoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]acetate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以62.6 mg的产率得到2-((2R,4aR,6S,7R,8aS)-2-phenyl-7-((E)-2-(phenylsulfonyl)vinyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)acetaldehyde
  参考文献：
  名称：

  SmI2-induced cyclization of (E)- and (Z)-β-alkoxyvinyl sulfones with aldehydes

  摘要：

  SmI2-induced reaction of (E)- and (Z)-beta-alkoxyvinyl sulfones onto an aldehyde function afforded 2,6-syn-2,3-trans- and 2,6-syn-2,3-cis-tetrahydropyran-3-ols, respectively, via stereoselective cyclization. This reaction was applied to the synthesis of 2-methyl-tetrahydropyran, corresponding to the N-ring of gymnocin-A, and 2-exo-methylene-tetrahydropyran, a key intermediate for convergent synthesis of polycyclic ethers based on the Suzuki-Miyaura reaction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.066