6,7,8-tri-O-acetyl-5,9-anhydro-1,4,10-trideoxy-L-glycero-L-talo-deco-2,3-diulose | 1021954-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,7,8-tri-O-acetyl-5,9-anhydro-1,4,10-trideoxy-L-glycero-L-talo-deco-2,3-diulose
• 英文别名: [(2S,3S,4R,5S,6S)-4,5-diacetyloxy-6-(2,3-dioxobutyl)-2-methyloxan-3-yl] acetate
• CAS: 1021954-32-4
• 化学式: C₁₆H₂₂O₉
• 分子量: 358.345
• InChiKey: HLKDXMBMCIOAAD-KRYVOKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6,7,8-tri-O-acetyl-5,9-anhydro-1,4,10-trideoxy-L-glycero-L-talo-deco-2,3-diulose 以 氯仿 为溶剂， 反应 1.0h， 以17%的产率得到(1S,4R,6S,7S,8R,9R)-7,8-bis(acetyloxy)-1-hydroxy-1,6-dimethyl-2-oxo-5-oxaspiro[3.5]non-9-yl acetate
  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：

  (1S)-2,3,4-tri-O-acetyl-1,5-anhydro-6,7,8,9-tetradeoxy-1-methyl-L-altro-non-7-ynitol 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到6,7,8-tri-O-acetyl-5,9-anhydro-1,4,10-trideoxy-L-glycero-L-talo-deco-2,3-diulose
  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