2(R),5(R)-di(hydroxymethyl)-3(S)-(uracil-1-yl)tetrahydrofuran | 798574-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2(R),5(R)-di(hydroxymethyl)-3(S)-(uracil-1-yl)tetrahydrofuran
• 英文别名: 1-[(2R,3R,5R)-2,5-bis(hydroxymethyl)oxolan-3-yl]pyrimidine-2,4-dione
• CAS: 798574-23-9
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 242.232
• InChiKey: ZHTMUPZIFNEQDQ-PRJMDXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 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：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2(R),5(R)-di(hydroxymethyl)-3(S)-(uracil-1-yl)tetrahydrofuran 在 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 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：

  (2R,3R,5R)-5-[1,3]Dioxolan-2-yl-2-trityloxymethyl-tetrahydro-furan-3-ylamine 在 盐酸 、 ammonium hydroxide 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 36.0h， 生成 2(R),5(R)-di(hydroxymethyl)-3(S)-(uracil-1-yl)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

文献信息

• Ring-expanded analogues of natural oxetanocin
  作者：Vasu Nair、Byoung-Kwon Chun、Jean John Vadakkan

  DOI：10.1016/j.tet.2004.08.087

  日期：2004.11

  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.