(1S,4S,6R,7S,8R)-7,8-bis(benzyloxy)-6-[(benzyloxy)methyl]-1-methyl-2-oxo-5-oxaspiro[3.5]nonan-1-ol | 1021954-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4S,6R,7S,8R)-7,8-bis(benzyloxy)-6-[(benzyloxy)methyl]-1-methyl-2-oxo-5-oxaspiro[3.5]nonan-1-ol
• CAS: 1021954-29-9
• 化学式: C₃₁H₃₄O₆
• 分子量: 502.607
• InChiKey: ZWJJFAPQPDBHBT-IXTQGANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 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 、 (1S,4S,6R,7S,8R)-7,8-bis(benzyloxy)-6-[(benzyloxy)methyl]-1-methyl-2-oxo-5-oxaspiro[3.5]nonan-1-ol 在 过碘酸 作用下， 反应 1.0h， 以63%的产率得到methyl 3-C-acetyl-3,7-anhydro-5,6,8-tri-O-benzyl-2,4-dideoxy-D-manno-octonate
  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：

  5,9-anhydro-7,8,10-tri-O-benzyl-1,4,6-trideoxy-D-manno-deco-2,3-diulose 以 氯仿 为溶剂， 反应 0.75h， 以46%的产率得到(1S,4S,6R,7S,8R)-7,8-bis(benzyloxy)-6-[(benzyloxy)methyl]-1-methyl-2-oxo-5-oxaspiro[3.5]nonan-1-ol
  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