(2R,3S,4aR,7R,8aS)-2-(hydroxymethyl)-6-methyleneoctahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal | 1246760-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2R,3S,4aR,7R,8aS)-2-(hydroxymethyl)-6-methyleneoctahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal
• 英文别名: (1S,3R,6R,8S,10R,13R)-12-methylidene-6-phenyl-2,5,7,11-tetraoxatricyclo[8.4.0.03,8]tetradecan-13-ol
• CAS: 1246760-30-4
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: YBEYSHZGUCRUJL-PHPOFCCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4aR,7R,8aS)-2-(hydroxymethyl)-6-methyleneoctahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到(2R,3S,4aR,7R,8aS)-7-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-6-methyleneoctahydropyrano[3,2-b]pyran-3-ol 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：

  (2R,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)hexahydropyrano[3,2-b]pyran-3(2H)-one benzylidene acetal 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 以78%的产率得到(2R,3S,4aR,7R,8aS)-2-(hydroxymethyl)-6-methyleneoctahydropyrano[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