O⁶-butyl-2'-deoxy-N²-isobutyrylguanosine | 82934-35-8

• 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: O⁶-butyl-2'-deoxy-N²-isobutyrylguanosine
• 英文别名: O⁶-butyl-2'-deoxy-N²-(2-methyl-1-oxopropyl)guanosine；N-[6-butoxy-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]-2-methylpropanamide
• CAS: 82934-35-8
• 化学式: C₁₈H₂₇N₅O₅
• 分子量: 393.443
• InChiKey: NCCBZWDUWHWTKQ-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  131.62
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  O⁶-butyl-2'-deoxy-N²-isobutyrylguanosine 在 ammonium hydroxide 作用下， 反应 72.0h， 以100%的产率得到O(6)-正丁基-2'-脱氧鸟苷
  参考文献：
  名称：

  Synthesis of -6-alkylated deoxyguanosine nucleosides

  摘要：

  DOI：

  10.1016/s0040-4039(00)87314-1
• 作为产物：
  描述：

  N²,3',5'-triisobutyryl-2'-deoxyguanosine 在 sodium ethanolate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 25.0h， 生成 O⁶-butyl-2'-deoxy-N²-isobutyrylguanosine
  参考文献：
  名称：

  Nucleotides, Part LXIII, New 2-(4-Nitrophenyl)ethyl(Npe)- and 2-(4-Nitrophenyl)ethoxycarbonyl(Npeoc)-Protected 2′-Deoxyribonucleosides and Their 3′-Phosphoramidites - Versatile Building Blocks for Oligonucleotide Synthesis

  摘要：

  A series of new base-protected and 5'-O-(4-monomethoxytrityl)- or 5'-O-(4,4'-dimethoxytrityl)-substituted 3'-(2-cyanoethyl diisopropylphosphoramidites) and 3'-[2-(4-nitrophenyl)ethyl diisopropylphosphoramidites] 52-66 and 67-82, respectively, are prepared as potential building blocks for oligonucleotide synthesis (see Scheme). Thus, 3',5'-di-O-acyl- and N-2,3'-O,5'-O-triacyl-2'-deoxyguanosines can easily be converted into the corresponding O-6-alkyl derivatives 6, 8, 10, 12, 14, and 16 by a Mitsunobu reaction using the appropriate alcohol. Mild hydrolysis removes the acyl groups from the sugar moiety (--> 9, 11, 13, 15, and 19 (via 18), resp.) which can then be tritylated (--> 38-42) and phosphitylated (--> 57-61) in the usual manner. N-2-[2-(4-nitrophenyl)ethoxycarbonyl]-substituted and N-2-[2-(4-nitrophenyl)ethoxycarbonyl]-O-6-[2-(4-nitrophenyl)ethyl]-substituted 2'-deoxyguanosines 5 and 7, respectively, are synthesized as new starting materials for tritylation (--> 28, 35, and 37) and phosphitylation (--> 54, 56, 70, and 78). Various O-4-alkylthymidines (see 20-24) are also converted to their 5'-O-dimethoxytrityl derivatives (see 43-47) and the corresponding phosphoramidites (see 62-66 and 79-82).

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2172::aid-hlca2172>3.0.co;2-r

文献信息

• TAKTAKISHVILI, M. O.;TABDZHUN, A.;PAATASHVILI, T. V., 14 MENDELEEV. SEZD PO OBSHCH. I PRIKL. XIMII, M.,(1989) S. 220
  作者：TAKTAKISHVILI, M. O.、TABDZHUN, A.、PAATASHVILI, T. V.

  DOI：——

  日期：——