methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside | 71695-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside
• 英文别名: [(2R,3S,4R,6R)-4-hydroxy-6-methoxy-2-methyloxan-3-yl] benzoate
• CAS: 71695-52-8
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: GBBTYIBCVJGZKH-OJAKKHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 methyl 4-O-benzoyl-3-bromo-2,3,6-trideoxy-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  A reactive intermediate formed by triflate rearrangement. A new displacement reaction for carbohydrate synthesis

  摘要：

  DOI：

  10.1021/jo00363a050
• 作为产物：
  描述：

  methyl 4-O-benzoyl-2,6-dideoxy-3-O-<(trifluoromethyl)sulfonyl>-β-D-ribo-hexopyranoside 在 四丁基亚硝酸铵 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以89%的产率得到methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Inversion of configuration in 2,6-dideoxy sugars. Triflate displacement by benzoate and nitrite anions

  摘要：

  Interconversion among 2,6-dideoxy sugars a room temperature has been accomplished in high yield. The eight possible methyl 3- and 4-O-benzoyl-2,6-dideoxy-beta-D-hexopyranosides 1-8 have been interconverted using their corresponding triflates as intermediates. Triflates derived from compounds 1, 2, 7, and 8 undergo internal displacement by the neighboring benzoyl group, inverting configuration at the triflyloxy-bearing carbon atom. Triflates of compounds 3-6 do not experience internal reaction; however, configuration was inverted in these compounds at room temperature by reaction with tetrabutylammonium nitrite. To illustrate the value of these reactions in oligosaccharide synthesis, configuration was inverted in three disaccharides composed of 2,6-dideoxy sugar residues.

  DOI：

  10.1021/jo00012a020

文献信息

• BINKLEY, ROGER W., J. ORG. CHEM., 56,(1991) N2, C. 3892-3896
  作者：BINKLEY, ROGER W.

  DOI：——

  日期：——
• Inversion of configuration in 2,6-dideoxy sugars. Triflate displacement by benzoate and nitrite anions
  作者：Roger W. Binkley

  DOI：10.1021/jo00012a020

  日期：1991.6

  Interconversion among 2,6-dideoxy sugars a room temperature has been accomplished in high yield. The eight possible methyl 3- and 4-O-benzoyl-2,6-dideoxy-beta-D-hexopyranosides 1-8 have been interconverted using their corresponding triflates as intermediates. Triflates derived from compounds 1, 2, 7, and 8 undergo internal displacement by the neighboring benzoyl group, inverting configuration at the triflyloxy-bearing carbon atom. Triflates of compounds 3-6 do not experience internal reaction; however, configuration was inverted in these compounds at room temperature by reaction with tetrabutylammonium nitrite. To illustrate the value of these reactions in oligosaccharide synthesis, configuration was inverted in three disaccharides composed of 2,6-dideoxy sugar residues.
• A reactive intermediate formed by triflate rearrangement. A new displacement reaction for carbohydrate synthesis
  作者：Roger W. Binkley、Matthew R. Sivik

  DOI：10.1021/jo00363a050

  日期：1986.6