2,6-anhydro-3,4,5-tri-O-[tert-butyl(dimethyl)silyl]-1,7,8,9-tetradeoxy-L-glycero-L-manno-non-8-enitol | 1021954-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-3,4,5-tri-O-[tert-butyl(dimethyl)silyl]-1,7,8,9-tetradeoxy-L-glycero-L-manno-non-8-enitol
• CAS: 1021954-57-3
• 化学式: C₂₇H₅₈O₄Si₃
• 分子量: 531.012
• InChiKey: XQMLMSUOZZGBRB-QCCYXRBGSA-N

物化性质

• 沸点：
  469.8±45.0 °C(predicted)
• 密度：
  0.91±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.52
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-3,4,5-tri-O-[tert-butyl(dimethyl)silyl]-1,7,8,9-tetradeoxy-L-glycero-L-manno-non-8-enitol 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到
  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：

  叔丁基二甲基氯硅烷 、 3-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-1-propene 在 氢氧化钾 、 silver nitrate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以61%的产率得到2,6-anhydro-3,4,5-tri-O-[tert-butyl(dimethyl)silyl]-1,7,8,9-tetradeoxy-L-glycero-L-manno-non-8-enitol
  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