methyl α-D-arabinofuranosyl-(1->3)-2,6-anhydro-3-C-hydroxymethyl-α-D-arabinofuranoside | 440359-16-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-D-arabinofuranosyl-(1->3)-2,6-anhydro-3-C-hydroxymethyl-α-D-arabinofuranoside
• 英文别名: (2R,3S,4S,5R)-2-(hydroxymethyl)-5-[[(1R,2R,4S,5S)-2-(hydroxymethyl)-4-methoxy-3,6-dioxabicyclo[3.2.0]heptan-1-yl]oxy]oxolane-3,4-diol
• CAS: 440359-16-0
• 化学式: C₁₂H₂₀O₉
• 分子量: 308.285
• InChiKey: WVGNZTXYRJCGLK-WFYUATTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl α-D-arabinofuranosyl-(1->3)-2,6-anhydro-3-C-hydroxymethyl-α-D-arabinofuranoside 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 6.0h， 生成 Acetic acid (1R,2R,4S,5S)-1-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-4-methoxy-3,6-dioxa-bicyclo[3.2.0]hept-2-ylmethyl ester
  参考文献：
  名称：

  Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis

  摘要：

  The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E-3 or E-O conformation is described. The E-3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the E-O-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by H-1 NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.

  DOI：

  10.1021/jo011127p
• 作为产物：
  描述：

  Acetic acid (1R,2R,4S,5S)-1-((2R,3S,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-4-methoxy-3,6-dioxa-bicyclo[3.2.0]hept-2-ylmethyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 methyl α-D-arabinofuranosyl-(1->3)-2,6-anhydro-3-C-hydroxymethyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis

  摘要：

  The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E-3 or E-O conformation is described. The E-3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the E-O-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by H-1 NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.

  DOI：

  10.1021/jo011127p