4-deoxy-4-(uracil-1'-yl)-2,5-anhydro-D-iditol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-deoxy-4-(uracil-1'-yl)-2,5-anhydro-D-iditol
• 英文别名: 2,5-Anhydro-3-deoxy-3-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-D-iditol；1-[(2S,3R,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]pyrimidine-2,4-dione
• 化学式: C₁₀H₁₄N₂O₆
• 分子量: 258.231
• InChiKey: NRJXZPWFUZOPTM-YGBUUZGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-脱水-d-甘露糖 在 吡啶 、 sodium tetrahydroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.0h， 生成 4-deoxy-4-(uracil-1'-yl)-2,5-anhydro-D-iditol
  参考文献：
  名称：

  Synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-d-mannitol: a novel class of hydroxymethyl-branched isonucleosides

  摘要：

  A concise synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-D-mannitol 6(a-d) has been achieved, using the deamination of 2-amino-2-deoxy-D-glucose to construct in one step the sugar skeleton with the desired sense of chirality at each asymmetric center. The selective dibenzoylation of 2,5-anhydro-D-mannitol 9 was investigated, and the key epoxide intermediate 13 was obtained in good yield via an intramolecular Mitsunobu reaction. The process of opening of epoxide 13 by nucleobases appeared to be regioselective. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00246-9

文献信息

• Synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-d-mannitol: a novel class of hydroxymethyl-branched isonucleosides
  作者：Z Lei、J.M Min、L.H Zhang

  DOI：10.1016/s0957-4166(00)00246-9

  日期：2000.7

  A concise synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-D-mannitol 6(a-d) has been achieved, using the deamination of 2-amino-2-deoxy-D-glucose to construct in one step the sugar skeleton with the desired sense of chirality at each asymmetric center. The selective dibenzoylation of 2,5-anhydro-D-mannitol 9 was investigated, and the key epoxide intermediate 13 was obtained in good yield via an intramolecular Mitsunobu reaction. The process of opening of epoxide 13 by nucleobases appeared to be regioselective. (C) 2000 Elsevier Science Ltd. All rights reserved.