8-azido-N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine | 328241-05-0

• 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: 8-azido-N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine
• 英文别名: N-[9-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(triethylsilyloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-8-azidopurin-6-yl]benzamide
• CAS: 328241-05-0
• 化学式: C₂₆H₃₄N₈O₅Si
• 分子量: 566.692
• InChiKey: VNWMMHRPQFXCAE-AGFSROSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  8-azido-N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine 在 palladium on activated charcoal C₅H₁₁ONO 、 氢气 、 碘 、 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N⁶-benzoyl-8-iodo-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine
  参考文献：
  名称：

  含核碱基主链的寡核苷，第 4 部分，乙炔二基连接的腺苷四聚体的收敛合成

  摘要：

  Deprotection of the tetramer 24, obtained by coupling the iodinated dimer 18 with the alkyne 23 gave the 8',5-ethynediyl-linked adenosine-derived tetramer 27 (Scheme 3). As direct iodination of C(5')-ethynylated adenosine derivatives failed, we prepared 18 via the 8-amino derivative 17 that was available by coupling the imine 15 with the iodide 7; 15, in its turn, was obtained from the 8-chloro derivative 12 via the 4-methoxybenzylamine 14 (Scheme 2). This method for the introduction of the S-iodo substituent was worked out with the N-benzoyladenosine 1 that was transformed into the azide 2 by lithiation and treatment with tosyl azide (Scheme I). Reduction of 2 led to the amine 3 that was transformed into 7 I,3-Dipolar cycloaddition of 3 and (trimethylsilyl)acetylene gave 6. The 8-substituted derivatives 4a-d were prepared similarly to 2, but could not be transformed into 7 The known chloride 8 was transformed into the iodide 11 via the amines 9 and 10. The amines 3, 10, and 16 form more or less completely persistent intramolecular C(8)N-H . . . O(5') H-bonds, while the dimeric amine 17 forms a ca. 50% persistent H-bond. There is no UV evidence for a base-base interaction in the protected and deprotected dimers and tetramers.

  DOI：

  10.1002/1522-2675(20001220)83:12<3229::aid-hlca3229>3.0.co;2-s
• 作为产物：
  描述：

  N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine 在 对甲苯磺酰叠氮 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 以84%的产率得到8-azido-N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine
  参考文献：
  名称：

  含核碱基主链的寡核苷，第 4 部分，乙炔二基连接的腺苷四聚体的收敛合成

  摘要：

  Deprotection of the tetramer 24, obtained by coupling the iodinated dimer 18 with the alkyne 23 gave the 8',5-ethynediyl-linked adenosine-derived tetramer 27 (Scheme 3). As direct iodination of C(5')-ethynylated adenosine derivatives failed, we prepared 18 via the 8-amino derivative 17 that was available by coupling the imine 15 with the iodide 7; 15, in its turn, was obtained from the 8-chloro derivative 12 via the 4-methoxybenzylamine 14 (Scheme 2). This method for the introduction of the S-iodo substituent was worked out with the N-benzoyladenosine 1 that was transformed into the azide 2 by lithiation and treatment with tosyl azide (Scheme I). Reduction of 2 led to the amine 3 that was transformed into 7 I,3-Dipolar cycloaddition of 3 and (trimethylsilyl)acetylene gave 6. The 8-substituted derivatives 4a-d were prepared similarly to 2, but could not be transformed into 7 The known chloride 8 was transformed into the iodide 11 via the amines 9 and 10. The amines 3, 10, and 16 form more or less completely persistent intramolecular C(8)N-H . . . O(5') H-bonds, while the dimeric amine 17 forms a ca. 50% persistent H-bond. There is no UV evidence for a base-base interaction in the protected and deprotected dimers and tetramers.

  DOI：

  10.1002/1522-2675(20001220)83:12<3229::aid-hlca3229>3.0.co;2-s

文献信息

• Oligonucleosides with a Nucleobase-Including Backbone, Part 4, A Convergent Synthesis of Ethynediyl-Linked Adenosine Tetramers
  作者：Hiroki Gunji、Andrea Vasella

  DOI：10.1002/1522-2675(20001220)83:12<3229::aid-hlca3229>3.0.co;2-s

  日期：2000.12.20

  Deprotection of the tetramer 24, obtained by coupling the iodinated dimer 18 with the alkyne 23 gave the 8',5-ethynediyl-linked adenosine-derived tetramer 27 (Scheme 3). As direct iodination of C(5')-ethynylated adenosine derivatives failed, we prepared 18 via the 8-amino derivative 17 that was available by coupling the imine 15 with the iodide 7; 15, in its turn, was obtained from the 8-chloro derivative 12 via the 4-methoxybenzylamine 14 (Scheme 2). This method for the introduction of the S-iodo substituent was worked out with the N-benzoyladenosine 1 that was transformed into the azide 2 by lithiation and treatment with tosyl azide (Scheme I). Reduction of 2 led to the amine 3 that was transformed into 7 I,3-Dipolar cycloaddition of 3 and (trimethylsilyl)acetylene gave 6. The 8-substituted derivatives 4a-d were prepared similarly to 2, but could not be transformed into 7 The known chloride 8 was transformed into the iodide 11 via the amines 9 and 10. The amines 3, 10, and 16 form more or less completely persistent intramolecular C(8)N-H . . . O(5') H-bonds, while the dimeric amine 17 forms a ca. 50% persistent H-bond. There is no UV evidence for a base-base interaction in the protected and deprotected dimers and tetramers.