2'-deoxy-O6-ethyl-N2,3'-O,5'-O-triisobutyrylguanosine | 259675-27-9

• 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: 2'-deoxy-O6-ethyl-N2,3'-O,5'-O-triisobutyrylguanosine
• 英文别名: 2'-deoxy-O⁶-ethyl-N²,3'-O,5'-O-triisobutyrylguanosine；2'-deoxy-O⁶-ethyl-N²-(2-methyl-1-oxopropyl)guanosine 3',5'-bis(2-methylpropanoate)
• CAS: 259675-27-9
• 化学式: C₂₄H₃₅N₅O₇
• 分子量: 505.571
• InChiKey: PLPXUQCDKZPNML-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  143.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-O6-ethyl-N2,3'-O,5'-O-triisobutyrylguanosine 在 sodium ethanolate 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-O⁶-ethyl-N²-isobutyrylguanosine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  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
• 作为产物：
  描述：

  乙醇 、 N²,3',5'-triisobutyryl-2'-deoxyguanosine 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以71%的产率得到2'-deoxy-O6-ethyl-N2,3'-O,5'-O-triisobutyrylguanosine
  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