(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 | 1021954-34-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 1021954-34-6
• 化学式: C₁₆H₂₂O₉
• 分子量: 358.345
• InChiKey: HHVODZDQWLJTLK-KJLPRMNKSA-N

反应信息

• 作为产物：
  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