Acetic acid (2R,3R,5R)-5-acetoxymethyl-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester | 798574-49-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: Acetic acid (2R,3R,5R)-5-acetoxymethyl-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS: 798574-49-9
• 化学式: C₁₄H₁₈N₂O₇
• 分子量: 326.306
• InChiKey: PQRGARFCEBDWMM-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  116.69
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,5R)-5-acetoxymethyl-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 在 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 三乙胺 、 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以45%的产率得到3(S)-(cytosin-1-yl)-2(R),5(R)-di(hydroxymethyl)tetrahydrofuran
  参考文献：
  名称：

  Ring-expanded analogues of natural oxetanocin

  摘要：

  Synthesis of ring-expanded analogs of the natural compound, oxetanocin is described. The starting material for the synthesis of the series, 4-7, was D-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, 8-11, the starting material was D-glucose and preparation of the key intermediate involved a rearrangement reaction. The structures of the target molecules were established by NMR, HRMS, optical rotation and UV data. Single-crystal X-ray data confirmed the enantiomeric structural assignments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.087
• 作为产物：
  描述：

  在 盐酸 、 ammonium hydroxide 、 sodium tetrahydroborate 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 37.0h， 生成 Acetic acid (2R,3R,5R)-5-acetoxymethyl-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Ring-expanded analogues of natural oxetanocin

  摘要：

  Synthesis of ring-expanded analogs of the natural compound, oxetanocin is described. The starting material for the synthesis of the series, 4-7, was D-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, 8-11, the starting material was D-glucose and preparation of the key intermediate involved a rearrangement reaction. The structures of the target molecules were established by NMR, HRMS, optical rotation and UV data. Single-crystal X-ray data confirmed the enantiomeric structural assignments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.087