(6R,7R,8S)-1-hydroxy-7,8-O-isopropylidene-6-methoxy-1-methyl-5-oxaspiro[3,4]octan-2-one | 1021954-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R,7R,8S)-1-hydroxy-7,8-O-isopropylidene-6-methoxy-1-methyl-5-oxaspiro[3,4]octan-2-one
• CAS: 1021954-75-5
• 化学式: C₁₂H₁₈O₆
• 分子量: 258.271
• InChiKey: NWLLADJDYFODQX-RORBGTHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (6R,7R,8S)-1-hydroxy-7,8-O-isopropylidene-6-methoxy-1-methyl-5-oxaspiro[3,4]octan-2-one 在 过碘酸 作用下， 反应 2.0h， 生成 dimethyl 4-C-acetyl-5-deoxy-2,3-O-isopropylidene-β-D-ribo-hexofuranosiduronate 、 dimethyl 4-C-acetyl-5-deoxy-2,3-O-isopropylidene-β-D-ribo-hexofuranosiduronate
  参考文献：
  名称：

  Stereocontrolled Photocyclization of 1,2-Diketones: Application of a 1,3-Acetyl Group Transfer Methodology to Carbohydrates

  摘要：

  Photolysis of 1-glycosyl-2,3-butanodione derivatives using visible light is a mild and selective procedure for the synthesis of chiral 1-hydroxy-1-methyl-5-oxaspiro[3.5]nonan-2-one carbohydrate derivatives. The results strongly suggest that stereocontrol of the cyclization is dependent on conformational and stereoelectronic factors. Further oxidative opening, of the 1-hydroxy-1-methyl-2-cyclobutanone moiety affords new C-ketoside derivatives either in C- and O-glycoside series. This tandem two-step process could be considered to be a stereocontrolled 1,3-transference of an acetyl group, and it can be applied either to pyranose and furanose models.

  DOI：

  10.1021/jo702663w
• 作为产物：
  描述：

  methyl 5,8-dideoxy-2,3-O-isopropylidene-β-D-ribo-octofuranoside-6,7-diulose 以 氯仿 为溶剂， 反应 1.0h， 以67%的产率得到(6R,7R,8S)-1-hydroxy-7,8-O-isopropylidene-6-methoxy-1-methyl-5-oxaspiro[3,4]octan-2-one
  参考文献：
  名称：

  Stereocontrolled Photocyclization of 1,2-Diketones: Application of a 1,3-Acetyl Group Transfer Methodology to Carbohydrates

  摘要：

  Photolysis of 1-glycosyl-2,3-butanodione derivatives using visible light is a mild and selective procedure for the synthesis of chiral 1-hydroxy-1-methyl-5-oxaspiro[3.5]nonan-2-one carbohydrate derivatives. The results strongly suggest that stereocontrol of the cyclization is dependent on conformational and stereoelectronic factors. Further oxidative opening, of the 1-hydroxy-1-methyl-2-cyclobutanone moiety affords new C-ketoside derivatives either in C- and O-glycoside series. This tandem two-step process could be considered to be a stereocontrolled 1,3-transference of an acetyl group, and it can be applied either to pyranose and furanose models.

  DOI：

  10.1021/jo702663w