ethyl 2-[(1R,2R,4R,5R,7R,10R)-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecan-5-yl]acetate | 741702-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: ethyl 2-[(1R,2R,4R,5R,7R,10R)-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecan-5-yl]acetate
• CAS: 741702-80-7
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: NPHVFYINMQJHDQ-LJFFPRQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(1R,2R,4R,5R,7R,10R)-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecan-5-yl]acetate 在 sodium azide 、 氯化铵 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 24.0h， 以96%的产率得到ethyl 2-[(2R,4aR,6R,7S,8S,8aS)-8-azido-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]acetate
  参考文献：
  名称：

  A Versatile and Stereocontrolled Route to Pyranose and Furanose C-Glycosides

  摘要：

  The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.

  DOI：

  10.1021/ol0490678
• 作为产物：
  描述：

  2-PROPENYL4,6-O-BENZYLIDENE-Α-D-GLUCOPYRANOSIDE2-丙烯基4,6-O-亚苄基-Α-D-吡喃葡萄糖苷 在 palladium diacetate 、 sodium hydride 、 二乙胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 ethyl 2-[(1R,2R,4R,5R,7R,10R)-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecan-5-yl]acetate
  参考文献：
  名称：

  A Versatile and Stereocontrolled Route to Pyranose and Furanose C-Glycosides

  摘要：

  The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.

  DOI：

  10.1021/ol0490678

文献信息

• A Versatile and Stereocontrolled Route to Pyranose and Furanose <i>C</i>-Glycosides
  作者：Joanne E. Harvey、Steven A. Raw、Richard J. K. Taylor

  DOI：10.1021/ol0490678

  日期：2004.7.1

  The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.