(4'R)-4,6-di-O-acetyl-1,2,3-trideoxy-2',3',4',5'-tetrahydro-4'-methyl-α-D-ribohexopyranoso<1,2-b>furan | 142344-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (4'R)-4,6-di-O-acetyl-1,2,3-trideoxy-2',3',4',5'-tetrahydro-4'-methyl-α-D-ribohexopyranoso<1,2-b>furan
• 英文别名: (4'R)-4,6-di-O-acetyl-1,2,3-trideoxy-2',3',4',5'-tetrahydro-4'-methyl-α-D-ribohexopyranoso[1,2-b]furan；[(3R,3aS,5S,6R,7aS)-5-acetyloxy-3-methyl-3,3a,4,5,6,7a-hexahydro-2H-furo[2,3-b]pyran-6-yl]methyl acetate
• CAS: 142344-31-8
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: ZBNAOEXGBPIONM-HADKEZEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,6-di-O-acetyl-1,2,3-trideoxy-2',3',4',5'-tetrahydro-4'-methylene-α-D-ribo-hexopyranoso<1,2-b>furan 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以79%的产率得到(4'R)-4,6-di-O-acetyl-1,2,3-trideoxy-2',3',4',5'-tetrahydro-4'-methyl-α-D-ribohexopyranoso<1,2-b>furan
  参考文献：
  名称：

  Moufid, Nadira; Chapleur, Yves; Mayon, Patrick, Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 999 - 1008

  摘要：

  DOI：

文献信息

• Stereocontrol in radical cyclizations on sugar templates
  作者：Catherine Lesueur、Robert Nouguier、Michéle Paula Bertrand、Pascale Hoffmann、Alain De Mesmaeker

  DOI：10.1016/s0040-4020(01)80694-3

  日期：1994.5

  The radical cyclization of alkyl hex-2-enopyranosides provides a stereocontrolled route to fused furanopyranes. The intermediate radical is generated either via the reduction of the appropriate halide by tin hydride or via sulfonyl radical addition to allyl hex-2-enopyranosides. The two methodologies are compared with respect to diastereoselectivity. Stereocontrol is discussed on the basis of conformational preference in the transition state.