(1S,4S,6S,7R,8S)-7,8-bis(benzyloxy)-1-hydroxy-6-methoxy-1-methyl-5-oxaspiro[3.5]nonan-2-one | 1021954-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,4S,6S,7R,8S)-7,8-bis(benzyloxy)-1-hydroxy-6-methoxy-1-methyl-5-oxaspiro[3.5]nonan-2-one
• 英文别名: (3S,4S,6S,7R,8S)-3-hydroxy-6-methoxy-3-methyl-7,8-bis(phenylmethoxy)-5-oxaspiro[3.5]nonan-2-one
• CAS: 1021954-22-2
• 化学式: C₂₄H₂₈O₆
• 分子量: 412.483
• InChiKey: PNAPSWDMTOZUKP-IBXSQZDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl (5S)-2,3-di-O-benzyl-4-deoxy-5-(2,3-dioxobutyl)-β-L-threo-pentopyranoside 以 氯仿 为溶剂， 反应 0.55h， 生成 (1S,4S,6S,7R,8S)-7,8-bis(benzyloxy)-1-hydroxy-6-methoxy-1-methyl-5-oxaspiro[3.5]nonan-2-one 、 (1R,4R,6S,7R,8S)-7,8-bis(benzyloxy)-1-hydroxy-6-methoxy-1-methyl-5-oxaspiro[3.5]nonan-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