(2R,3S,4aR,6S,7R,8aS)-7-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-6-methyloctahydropyrano[3,2-b]pyran-3-ol | 1246760-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-6-methyloctahydropyrano[3,2-b]pyran-3-ol
• 英文别名: (2S,3R,4aS,6R,7S,8aR)-3-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-2-methyl-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-7-ol
• CAS: 1246760-28-0
• 化学式: C₁₆H₃₂O₅Si
• 分子量: 332.513
• InChiKey: WVTYVQGMHKLSHS-JRULLXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,3S,4aR,6R,7R,8aS)-7-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3-ol benzylidene acetal 在 乙醇 作用下， 以83%的产率得到(2R,3S,4aR,6S,7R,8aS)-7-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-6-methyloctahydropyrano[3,2-b]pyran-3-ol
  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