Benzoic acid (2R,3R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-yl ester | 647021-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Benzoic acid (2R,3R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-yl ester
• CAS: 647021-61-2
• 化学式: C₃₀H₃₆O₅Si
• 分子量: 504.698
• InChiKey: RMCLVJCVWBEICG-FCEKVYKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以95%的产率得到(2R,3R,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-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
• 作为产物：
  描述：

  2-萘甲醇 在 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 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