(2R,4aR,5aS,8aS,9S,9aR)-5a-methoxy-7-oxo-2-phenyloctahydrofuro[2',3':5,6]pyrano[3,2-d][1,3]dioxin-9-yl acetate | 1423010-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (2R,4aR,5aS,8aS,9S,9aR)-5a-methoxy-7-oxo-2-phenyloctahydrofuro[2',3':5,6]pyrano[3,2-d][1,3]dioxin-9-yl acetate
• 英文别名: [(1R,3S,7S,8S,9R,11R)-3-methoxy-5-oxo-11-phenyl-2,6,10,12-tetraoxatricyclo[7.4.0.03,7]tridecan-8-yl] acetate
• CAS: 1423010-15-4
• 化学式: C₁₈H₂₀O₈
• 分子量: 364.352
• InChiKey: SRXIUYQHCDPJEJ-YYOXGBMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 3-O-acetyl-4,6-O-benzylidene-2-O-diazoacetyl-α-D-mannopyranoside 在 dirhodium tetraacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 以90%的产率得到(2R,4aR,5aS,8aS,9S,9aR)-5a-methoxy-7-oxo-2-phenyloctahydrofuro[2',3':5,6]pyrano[3,2-d][1,3]dioxin-9-yl acetate
  参考文献：
  名称：

  Gram-Scale Quaternarization of the Anomeric Position of Carbohydrates: Dramatic Effects of Molecular Sieves on Rhodium(II)-Mediated Decomposi­tion of Diazo Sugars

  摘要：

  The optimization of rhodium(II) carbene mediated quaternarization of the anomeric position of carbohydrates is reported. Preparation of ketopyranosides in good and reliable yields requires reverse addition of the substrate to a highly diluted suspension of the catalyst in refluxing 1,2-dichloroethane, as well as addition of a carefully controlled amount of molecular sieves, and vigorous stirring. Following these optimized reaction conditions, functionalization of the anomeric position of carbohydrates can finally be performed on a preparative scale.

  DOI：

  10.1055/s-0032-1317013