(2R,3S,6S)-2-Hydroxymethyl-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-ol | 647021-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S,6S)-2-Hydroxymethyl-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-ol
• CAS: 647021-59-8
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: HQSIGIOLHDFBNU-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,6S)-2-Hydroxymethyl-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-ol 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Benzoic acid (2R,3R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Trichloro-oxazolines as Activated Donors for Aminosugar Coupling

  摘要：

  [GRAPHICS]Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions.

  DOI：

  10.1021/ol0359620
• 作为产物：
  描述：

  2-萘甲醇 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 (2R,3S,6S)-2-Hydroxymethyl-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  Trichloro-oxazolines as Activated Donors for Aminosugar Coupling

  摘要：

  [GRAPHICS]Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions.

  DOI：

  10.1021/ol0359620