1,5-anhydro-2,3-O-bis-pivaloyl-D-glucitol | 221278-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2,3-O-bis-pivaloyl-D-glucitol
• 英文别名: 1,5-anhydro-2,3-dipivaloyl-D-glucitol；[(3S,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-5-hydroxy-6-(hydroxymethyl)oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 221278-40-6
• 化学式: C₁₆H₂₈O₇
• 分子量: 332.394
• InChiKey: XJGWKVYMIZLEJL-WRWGMCAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,3-O-bis-pivaloyl-D-glucitol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成
  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：

  2,6-脱水-1,3-O-亚苄基己糖醇 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 216.0h， 生成 1,5-anhydro-2,3-O-bis-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

文献信息

• A short and efficient synthesis of 1,5-anhydro-d-glucitol 6-phosphate
  作者：Changyou Yuan、Rawle I. Hollingsworth

  DOI：10.1016/j.tetlet.2011.07.082

  日期：2011.10

  of the hydroxyl groups as their allyl ether followed by reductive cleavage of the glycosidic linkage with triethylsilane formed the protected anhydroglucitol. No ring rearrangement or ring contraction was observed during the reduction step. Using the PdCl2–CuCl2–activated charcoal system, the allyl ether bond was cleaved with a low loading of the catalyst (0.0025 equiv per allyl group). 1,5-Anhydro-d-glucitol

  由甲基-d-葡糖苷以高收率和纯度制备重要的d-葡萄糖和d-葡萄糖6-磷酸类似物1，5-脱水-d-葡萄糖醇和1，5-脱水-d-葡萄糖醇6-磷酸。保护羟基作为它们的烯丙基醚，然后用三乙基硅烷还原性切割糖苷键，形成了被保护的脱水葡萄糖醇。在还原步骤中未观察到环重排或环收缩。使用PdCl 2 -CuCl 2活化的木炭系统，烯丙基醚键在低催化剂负载量（每个烯丙基0.0025当量）的作用下断裂。通过将1，5-脱水-d-葡萄糖醇磷酸化来制备1，5-脱水-d-葡萄糖醇6-磷酸。