methyl 2,6-anhydro-3-C-hydroxymethyl-α-D-arabinofuranoside | 440359-20-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-anhydro-3-C-hydroxymethyl-α-D-arabinofuranoside
• 英文别名: (1R,2R,4S,5S)-2-(hydroxymethyl)-4-methoxy-3,6-dioxabicyclo[3.2.0]heptan-1-ol
• CAS: 440359-20-6
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: YRMWCVXJNHSVRW-MVIOUDGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,6-anhydro-3-C-hydroxymethyl-α-D-arabinofuranoside 在 三氟甲磺酸酐 、 4 A molecular sieve 、 di-tert-butylmethylpyridine 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 21.08h， 生成
  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：

  methyl 3-O-benzyl-2,5-bis-O-di-tert-butylsilyl-α-D-arabinofuranoside 在 palladium dihydroxide 咪唑 、 ruthenium trichloride 、 sodium periodate 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 氢氟酸 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 sodium acetate 、 potassium carbonate 、 对甲苯磺酸 、 barium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 162.5h， 生成 methyl 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