3(R)-(adenin-9-yl)-2(S),5(S)-di(hydroxymethyl)tetrahydrofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3(R)-(adenin-9-yl)-2(S),5(S)-di(hydroxymethyl)tetrahydrofuran
• 英文别名: [(2S,4S,5S)-4-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-2-yl]methanol
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: BNCGXWUHFHKRDK-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(trityloxymethyl)tetrahydrofuran 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 45.0h， 生成 3(R)-(adenin-9-yl)-2(S),5(S)-di(hydroxymethyl)tetrahydrofuran
  参考文献：
  名称：

  RING-EXPANDED ANALOGUES OF NATURAL OXETANOCIN: (+) AND (−) HYDROXYMETHYL ISODIDEOXYADENOSINE

  摘要：

  New enantiomeric isonucleoside analogues related to natural oxetanocin have been synthesized from D-glucosamine and D-glucose. The structures of the target compounds were confirmed 4 NMR, HRMS, UV single crystal X-ray, and optical rotation data. Stability studies with respect to purine nucleoside phosphorylase and adenosine deaminase show that these compounds are not substrates. Antiviral results are discussed.

  DOI：

  10.1081/ncn-200060036

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.
• RING-EXPANDED ANALOGUES OF NATURAL OXETANOCIN: (+) AND (−) HYDROXYMETHYL ISODIDEOXYADENOSINE
  作者：Byoung-Kwon Chun、Jean John Vadakkan、Vasu Nair

  DOI：10.1081/ncn-200060036

  日期：2005.4.1

  New enantiomeric isonucleoside analogues related to natural oxetanocin have been synthesized from D-glucosamine and D-glucose. The structures of the target compounds were confirmed 4 NMR, HRMS, UV single crystal X-ray, and optical rotation data. Stability studies with respect to purine nucleoside phosphorylase and adenosine deaminase show that these compounds are not substrates. Antiviral results are discussed.