(2R,3S,4S,6S)-6-(benzyloxy)-2-methyltetrahydro-2H-pyran-3,4-diol | 117399-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,6S)-6-(benzyloxy)-2-methyltetrahydro-2H-pyran-3,4-diol
• 英文别名: (2R,3S,4S,6S)-2-methyl-6-phenylmethoxyoxane-3,4-diol
• CAS: 117399-41-4
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: HKVKPOJNFRNEJA-LPTSXCQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3aR,4R,6S,7aS)-6-(benzyloxy)-4-methyltetrahydro-3aH-[1,3]-dioxolo[4,5-c]pyran-2-one 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到(2R,3S,4S,6S)-6-(benzyloxy)-2-methyltetrahydro-2H-pyran-3,4-diol
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of an α-6-Deoxyaltropyranoside as Well as its 2-/3-Deoxy and 2,3-Dideoxy Congeners

  摘要：

  A highly divergent de novo asymmetric synthesis of benzyl alpha-6-deoxyaltropyranoside, benzyl alpha-ascarylopyranoside, benzyl alpha-amicetopyranoside, and benzyl a-digitoxopyranoside has been achieved via I common pyranone intermediate. The routes rely upon it palladium(0)-catalyzed glycosylation reaction and corresponding post-glycosylation transformations, The control of the absolute and relative stereochemical configuration came from a Noyori reduction of 2-acylfuran and subsequent diastereoselective introduction of other stereogenic centers.

  DOI：

  10.1021/jo9009722

文献信息

• BINKLEY, ROGER W.;SCHNEIDER, J. STEVEN, J. CARBOHYDR. CHEM., 7,(1988) N 1, 157-167
  作者：BINKLEY, ROGER W.、SCHNEIDER, J. STEVEN

  DOI：——

  日期：——