(2S,3R,4R,5S)-2,3-anhydro-5-O-benzyl-4-methyl-1,2,3,5-hexanetetrol | 136864-20-5

• 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: (2S,3R,4R,5S)-2,3-anhydro-5-O-benzyl-4-methyl-1,2,3,5-hexanetetrol
• CAS: 136864-20-5
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: NWEUECNPFCYZJA-IMIFBBOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  三甲基铝 、 benzyl 2,3-anhydro-4-O-(tert-butyldimethylsilyl)-β-L-ribopyranoside 生成 (2S,3R,4R,5S)-2,3-anhydro-5-O-benzyl-4-methyl-1,2,3,5-hexanetetrol 、 (2S,3R,4R,5R)-2,3-anhydro-5-O-benzyl-4-methyl-1,2,3,5-hexanetetrol
  参考文献：
  名称：

  Organoaluminium induced ring-opening of epoxypyranosides. IV. Synthesis and structure of γ- hydroxy-lsoleucine stereoisomers and their corresponding lactones.

  摘要：

  Two gamma- hydroxy-isoleucine stereoisomers 8 (2R, 3R, 4R), and 14 (2S, 3R, 4R) as well as their corresponding gamma- lactones 9 and 15 were synthesized using a tandem, Me3Al induced opening of the epoxide and pyranoside rings of benzyl 2,3-anhydro-4-O-(tert-butyldimethylsilyl)-beta-L-ribopyranoside (1). The structure of the lactone hydrochloride 9 was confirmed by an X-ray crystal structure determination.

  DOI：

  10.1016/s0040-4020(01)86574-1