1,5-anhydro-3-O-pivaloyl-D-glucitol | 221278-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-3-O-pivaloyl-D-glucitol
• 英文别名: [(2R,3R,4R,5S)-3,5-dihydroxy-2-(hydroxymethyl)oxan-4-yl] 2,2-dimethylpropanoate
• CAS: 221278-34-8
• 化学式: C₁₁H₂₀O₆
• 分子量: 248.276
• InChiKey: AJBAVRJGHWPIOW-JQCXWYLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.94
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  96.22
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-3-O-pivaloyl-D-glucitol 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 tetrabutylammonium salt of adenine 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 50.0h， 生成 1,5-anhydro-6-O-monomethoxytrityl-3-O-pivaloyl-4-deoxy-D-mannitol
  参考文献：
  名称：

  Synthesis and Conformational Analysis of 1,5-Anhydro-2,4-dideoxy-D-mannitol Nucleosides

  摘要：

  1,5-Anhydro-4,6-O-benzylidene-D-glucitol was used as starting material for the synthesis of 1,5-anhydro-2,4-dideoxy-D-mannitol nucleosides with an adenine and uracil base moiety. The compound with a purine base was obtained by direct nucleophilic substitution of a triflate. The pyrimidine nucleoside could be obtained by epoxide opening followed by inversion of configuration at the 3'-position. Both nucleosides adopt a C1 conformation with an axial base moiety.

  DOI：

  10.1080/15257779908043064
• 作为产物：
  描述：

  1,5-anhydro-4,6-O-benzylidene-3-O-pivaloyl-2-O-tert-butyldimethylsilyl-D-glucitol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以73%的产率得到1,5-anhydro-3-O-pivaloyl-D-glucitol
  参考文献：
  名称：

  Synthesis and Conformational Analysis of 1,5-Anhydro-2,4-dideoxy-D-mannitol Nucleosides

  摘要：

  1,5-Anhydro-4,6-O-benzylidene-D-glucitol was used as starting material for the synthesis of 1,5-anhydro-2,4-dideoxy-D-mannitol nucleosides with an adenine and uracil base moiety. The compound with a purine base was obtained by direct nucleophilic substitution of a triflate. The pyrimidine nucleoside could be obtained by epoxide opening followed by inversion of configuration at the 3'-position. Both nucleosides adopt a C1 conformation with an axial base moiety.

  DOI：

  10.1080/15257779908043064