phenyl (9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate | 1373396-62-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: phenyl (9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate
• 英文别名: N⁶-benzoyl 2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)adenosine
• CAS: 1373396-62-3
• 化学式: C₂₆H₃₅N₅O₆Si
• 分子量: 541.679
• InChiKey: DPVBAUJJMLLCLM-ZDXOVATRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  118.85
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  phenyl (9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate 、 氯甲酸甲酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以89%的产率得到N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-8-carboxymethyladenosine
  参考文献：
  名称：

  Hydrogen-Bonding Complexes of 5-Azauracil and Uracil Derivatives in Organic Medium

  摘要：

  Uracil derivatives form strong complexes with complementary 2,4-diaminotriazine and adenine compounds, whereas derivatives of 5-azauracil (2,4-dioxotriazine) are known to form weak complexes in aqueous medium. However, herein we report that in organic medium (CDCl3), the 5-azauracil moiety forms hydrogen-bond-mediated complexes with complementary 2,4-diaminotriazine and adenine compounds, with strengths comparable to those formed by uracil compounds. Such dichotomous base-pairing behavior of the 5-azauracil moiety, in organic versus aqueous media, is found to be consistent with the ionization of the 5-azauracil moiety in aqueous medium leading to competitive interference from water molecules (via solvation), which is absent (lack of such ionization and solvent interference) in organic medium. This discriminating role of solvent (e.g., water) could have been an important factor in the selection of molecules, based on their physicochemical properties, and subsequently in the emergence of potential primordial informational oligomers that would have played a role in the origins of life.

  DOI：

  10.1021/acs.joc.5b00911
• 作为产物：
  描述：

  腺苷 在 咪唑 、 N-甲基咪唑 、 高氯酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 31.0h， 生成 phenyl (9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate
  参考文献：
  名称：

  Exo-N-氨基甲酰基核苷的高效合成：在氨基磷酸酯前药合成中的应用

  摘要：

  利用N-甲基咪唑 (NMI)开发了一种使用各种氯甲酸酯对嘌呤核苷的 6-外-氨基基团的有效保护方案。腺苷类似物1的外型- N 6 -基团与氯甲酸烷基酯/和芳基氯甲酸酯在优化条件下的反应提供了N 6 -氨基甲酰基腺苷 ( 2a – j ) 的良好收率。的反应Ñ 6 -Cbz保护的核苷（5A - ç用苯基磷酰氯（）7）使用吨-BuMgCl 然后催化氢化以优异的产率提供相应的氨基磷酸酯前核苷酸（8a - c）。

  DOI：

  10.1021/ol300777p