Acetic acid (2S,6R)-6-acetoxymethyl-4-oxo-tetrahydro-pyran-2-ylmethyl ester | 183952-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: Acetic acid (2S,6R)-6-acetoxymethyl-4-oxo-tetrahydro-pyran-2-ylmethyl ester
• 英文别名: [(2R,6S)-6-(acetyloxymethyl)-4-oxooxan-2-yl]methyl acetate
• CAS: 183952-47-8
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: JWTIYJWLGUKFTK-PHIMTYICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,6R)-6-acetoxymethyl-4-oxo-tetrahydro-pyran-2-ylmethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 phosphate buffer 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 43.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2S,6R)-6-acetoxymethyl-4-oxo-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Lipase mediated desymmetrization of meso-2,6-di(acetoxymethyl)-tetrahydropyran-4-one derivatives. An innovative route to enantiopure 2,4,6-trifunctionalized C-glycosides

  摘要：

  The desymmetrization of several meso-configurated 2,4,6-trifunctionalized tetrahydropyrans was studied. Amongst the derivatives investigated the conformationally more rigid spiro ketal 8b afforded hydroxy-acetate (-)-12 in excellent chemical yield and enantiomeric excess. The absolute configuration of the resulting 2,4,6-trifunctionalized C-glycosides was established by X-ray crystal diffraction. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00380-1
• 作为产物：
  描述：

  ((8R,10S)-10-Hydroxymethyl-3,3-dimethyl-1,5,9-trioxa-spiro[5.5]undec-8-yl)-methanol 在 吡啶 、 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 作用下， 以 丙酮 为溶剂， 反应 71.0h， 生成 Acetic acid (2S,6R)-6-acetoxymethyl-4-oxo-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Lipase mediated desymmetrization of meso-2,6-di(acetoxymethyl)-tetrahydropyran-4-one derivatives. An innovative route to enantiopure 2,4,6-trifunctionalized C-glycosides

  摘要：

  The desymmetrization of several meso-configurated 2,4,6-trifunctionalized tetrahydropyrans was studied. Amongst the derivatives investigated the conformationally more rigid spiro ketal 8b afforded hydroxy-acetate (-)-12 in excellent chemical yield and enantiomeric excess. The absolute configuration of the resulting 2,4,6-trifunctionalized C-glycosides was established by X-ray crystal diffraction. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00380-1