1,6-Anhydro-2-O-benzoyl-4-deoxy-4-β-D-glucopyranose | 144542-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-Anhydro-2-O-benzoyl-4-deoxy-4-β-D-glucopyranose
• 英文别名: [(1S,3S,4R,5R)-3-hydroxy-6,8-dioxabicyclo[3.2.1]octan-4-yl] benzoate
• CAS: 144542-87-0
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: TUNSOKAHCWUIRN-MEWQQHAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  1,6-Anhydro-2-O-benzoyl-4-deoxy-4-β-D-glucopyranose 在 吡啶 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 1,6:2,3-Dianhydro-4-deoxy-β-D-ribo-hexopyranose
  参考文献：
  名称：

  Reactions of some pyranoside diol monotriflates with nucleophiles and bases

  摘要：

  Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and ''epimerized'' pyranosides, particularly where a fused acetal ring inhibits ring contraction. Among the substrates examined (1, 2,3,4,35), only 4 shows a strong tendency to give ring-contracted products. The reaction of 1-3 with more basic nucleophiles (F-, t-BuO-) leads to the anhydrosugars 8, 25, and 26, respectively. The S(N)2 reaction of 35 with tetra-n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.

  DOI：

  10.1021/jo00052a058
• 作为产物：
  描述：

  1,-脱水-3,-O-异丙二烯-β-D-谷氨酸五乙酸酯 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 四丁基碘化铵 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.17h， 生成 1,6-Anhydro-2-O-benzoyl-4-deoxy-4-β-D-glucopyranose
  参考文献：
  名称：

  Reactions of some pyranoside diol monotriflates with nucleophiles and bases

  摘要：

  Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and ''epimerized'' pyranosides, particularly where a fused acetal ring inhibits ring contraction. Among the substrates examined (1, 2,3,4,35), only 4 shows a strong tendency to give ring-contracted products. The reaction of 1-3 with more basic nucleophiles (F-, t-BuO-) leads to the anhydrosugars 8, 25, and 26, respectively. The S(N)2 reaction of 35 with tetra-n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.

  DOI：

  10.1021/jo00052a058

文献信息

• Reactions of some pyranoside diol monotriflates with nucleophiles and bases
  作者：Spencer Knapp、Andrew B. J. Naughton、Carlos Jaramillo、Brenda Pipik

  DOI：10.1021/jo00052a058

  日期：1992.12

  Reaction of pyranoside diol (equatorial) monotriflates with soft, nonbasic nucleophiles is a useful way to make axial heteroatom-substituted and ''epimerized'' pyranosides, particularly where a fused acetal ring inhibits ring contraction. Among the substrates examined (1, 2,3,4,35), only 4 shows a strong tendency to give ring-contracted products. The reaction of 1-3 with more basic nucleophiles (F-, t-BuO-) leads to the anhydrosugars 8, 25, and 26, respectively. The S(N)2 reaction of 35 with tetra-n-butylammonium iodide forms the basis for a new synthesis of the Cerny epoxide 32.