(SR)-4-[(adenin-9-yl)-tetrahydrofuran-2,2-diyl]dimethanol | 918952-73-5

• 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: (SR)-4-[(adenin-9-yl)-tetrahydrofuran-2,2-diyl]dimethanol
• 英文别名: (+/-)-2',3'-dideoxy-4'-hydroxymethyl-iso-adenosine；4-[(adenin-9-yl)-tetrahydrofuran-2,2-diyl]dimethanol；[4-(6-Amino-9H-purin-9-yl)oxolane-2,2-diyl]dimethanol；[4-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-2-yl]methanol
• CAS: 918952-73-5
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: NZQGNBXWOVQCCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 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：

  5-(3-hydroxyprop-1-ynyl)-2,2-dimethyl-1,3-dioxan-5-ol 在 Pd-BaSO₄ 咪唑 、 喹啉 、 偶氮二异丁腈 、 四丁基氟化铵 、 氨 、 氢气 、 三正丁基氢锡 、 sodium methylate 、 溶剂黄146 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 27.5h， 生成 (SR)-4-[(adenin-9-yl)-tetrahydrofuran-2,2-diyl]dimethanol
  参考文献：
  名称：

  New Synthesis of (±)-Isonucleosides

  摘要：

  A novel method for synthesizing isonucleosides, a new class of anti-HIV nucleosides, is described. 2,2- Dimethyl- 1,3- dioxan- 5- one was converted into a dioxabicyclohexane derivative in six steps. After cleaving the epoxide group with thiophenol, the resulting product was subjected to the Mitsunobu reaction in the presence of a nucleobase to give the desired isonucleoside derivative via migration of the thiophenyl group. Removal of the thiophenyl group under radical conditions followed by deprotection led to the 4'- substituted 2', 3'- dideoxyisonucleosides as a racemic mixture.

  DOI：

  10.1021/ol062491j

文献信息

• Design and Synthesis of Isonucleosides Constructed on a 2-Oxa-6-thiabicyclo[3.2.0]heptane Scaffold
  作者：Yuichi Yoshimura、Kazuhiro Asami、Tomozumi Imamichi、Tomoko Okuda、Kimiyasu Shiraki、Hiroki Takahata

  DOI：10.1021/jo100556u

  日期：2010.6.18

  other hand, was converted into the corresponding dimesylate, which was then treated with mercury acetate and trifluoroacetic acid to remove the PMB group. The resulting thiol derivative was treated with DBU to give the desired isonucleoside constructed on a 2-oxa-6-thiobicyclo[3.2.0]heptane scaffold after deprotection. The optimized conformer of the isonucleoside was calculated using DFT at the B3LYP/6-31G**

  描述了一种设计和合成含有2-oxa-6-硫代双环[3.2.0]庚烷骨架的异核苷的新方法。2,2-二甲基-1,3-二恶烷-5-酮13通过六个步骤将其转化为二氧杂双环己烷衍生物。用硫醇（硫酚或PMB硫醇）切割环氧基后，将所得产物在核碱基存在下进行Mitsunobu反应。反应通过硫代硫醚基团的迁移进行，得到所需的异核苷衍生物。在苯基硫化物衍生物的情况下，自由基脱硫，然后脱保护，得到4'-取代的2'，3'-二脱氧异核苷。另一方面，将PMB硫化物衍生物转化为相应的二甲基磺酸酯，然后将其用乙酸汞和三氟乙酸处理以除去PMB基团。用DBU处理所得的硫醇衍生物，得到脱保护后在2-氧杂-6-硫代双环[3.2.0]庚烷骨架上构建的所需异核苷。
• New Synthesis of (±)-Isonucleosides
  作者：Yuichi Yoshimura、Kazuhiro Asami、Hiromitsu Matsui、Hiromichi Tanaka、Hiroki Takahata

  DOI：10.1021/ol062491j

  日期：2006.12.1

  A novel method for synthesizing isonucleosides, a new class of anti-HIV nucleosides, is described. 2,2- Dimethyl- 1,3- dioxan- 5- one was converted into a dioxabicyclohexane derivative in six steps. After cleaving the epoxide group with thiophenol, the resulting product was subjected to the Mitsunobu reaction in the presence of a nucleobase to give the desired isonucleoside derivative via migration of the thiophenyl group. Removal of the thiophenyl group under radical conditions followed by deprotection led to the 4'- substituted 2', 3'- dideoxyisonucleosides as a racemic mixture.