(2R,3S,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3-yl acetate benzylidene acetal | 1246760-23-5

• 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: (2R,3S,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3-yl acetate benzylidene acetal
• 英文别名: [(1S,3R,6R,8S,10R,12R,13S)-12-(benzenesulfonylmethyl)-6-phenyl-2,5,7,11-tetraoxatricyclo[8.4.0.03,8]tetradecan-13-yl] acetate
• CAS: 1246760-23-5
• 化学式: C₂₅H₂₈O₈S
• 分子量: 488.559
• InChiKey: ZEWMEVCPVRDMIE-TYSQMLMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-((2R,4aR,6S,7R,8aS)-2-phenyl-7-((Z)-2-(phenylsulfonyl)vinyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)acetaldehyde 、 乙酸酐 在 甲醇 、 samarium diiodide 、 吡啶 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到(2R,3S,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3-yl acetate 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