2'-deoxy-O⁶-<2-(phenylsulfonyl)ethyl>guanosine | 187674-25-5

• 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-<2-(phenylsulfonyl)ethyl>guanosine
• 英文别名: 2'-deoxy-O⁶-[2-(phenylsulfonyl)ethyl]guanosine；(2R,3S,5R)-5-[2-amino-6-[2-(benzenesulfonyl)ethoxy]purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 187674-25-5
• 化学式: C₁₈H₂₁N₅O₆S
• 分子量: 435.461
• InChiKey: DEKSLDRLCGDYJO-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  171
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-deoxy-O⁶-<2-(phenylsulfonyl)ethyl>guanosine 在 吡啶 、 氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 17.13h， 生成 5-O-(4,4-二甲氧基三苯甲游基)-2-脱氧鸟苷
  参考文献：
  名称：

  Nucleotides, Part LXI, Phthaloyl Strategy: A New Concept of Oligonucleotide Synthesis

  摘要：

  A new alternative strategy of oligonucleotide synthesis was developed by use of thr phthaloyl protecting group for the exocyclic amino functions of the nucleobases (see 9 - 12). This approach combines the advantages of cheap and easily accessable monomeric building blocks (see 17 - 20), standard machine-aided oligonucleotide synthesis, and a fast deprotection protocol which is orthogonal to the cleavage procedure from the solid support. The crude oligonucleotides show high purity and require, in general, no further chromatographic purification.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<633::aid-hlca633>3.0.co;2-u
• 作为产物：
  描述：

  3',5'-di-O-acetyl-2'-deoxyguanosine 在 ammonium hydroxide 、 ethyl azodicarboxylate 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 2'-deoxy-O⁶-<2-(phenylsulfonyl)ethyl>guanosine
  参考文献：
  名称：

  Nucleotides, Part LXI, Phthaloyl Strategy: A New Concept of Oligonucleotide Synthesis

  摘要：

  A new alternative strategy of oligonucleotide synthesis was developed by use of thr phthaloyl protecting group for the exocyclic amino functions of the nucleobases (see 9 - 12). This approach combines the advantages of cheap and easily accessable monomeric building blocks (see 17 - 20), standard machine-aided oligonucleotide synthesis, and a fast deprotection protocol which is orthogonal to the cleavage procedure from the solid support. The crude oligonucleotides show high purity and require, in general, no further chromatographic purification.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<633::aid-hlca633>3.0.co;2-u

文献信息

• Nucleotides, Part LXVII, The 2-Cyanoethyl and (2-Cyanoethoxy)carbonyl Group for Base Protection in Nucleoside and Nucleotide Chemistry
  作者：Claudia Merk、Tilman Reiner、Evgeny Kvasyuk、Wolfgang Pfleiderer

  DOI：10.1002/1522-2675(20001220)83:12<3198::aid-hlca3198>3.0.co;2-q

  日期：2000.12.20

  The amino functions of the common 2′-deoxyribo- and ribonucleosides were blocked by the (2-cyanoethoxy)carbonyl group on treatment with 2-cyanoethyl carbonochloridate (5) or 1-[(2-cyanoethoxy)carbonyl]-3-methyl-1H-imidazolium chloride (6) leading to 7, 18, 8, 19, 9, and 20. In 2′-deoxyguanosine, the amide group was additionally blocked at the O6 position by the 2-cyanoethyl (27) and 2-(4-nitrophenyl)ethyl

  在用 2-氰基乙基碳氯酸酯 (5) 或 1-[(2-氰基乙氧基)羰基]-3-甲基-处理时，常见的 2'-脱氧核糖和核糖核苷的氨基官能团被 (2-氰基乙氧基)羰基封闭。 1H-咪唑氯化物 (6) 产生 7, 18, 8, 19, 9 和 20。在 2'-脱氧鸟苷中，酰胺基团在 O6 位被 2-氰乙基 (27) 和 2-( 4-硝基苯基)乙基(31, 32)。关于通过 β-消除裂解 ce/ceoc 和 npe/npeoc 基团的比较动力学研究揭示了有关核碱基不同位点的各种封闭基团的容易性和顺序脱保护的有价值的信息。
• Nucleotides. Part L. Aglycone protection by the (2-dansylethoxy)carbonyl (= {2-{[5-(dimethylamino)naphthalen-l-yl]sulfonyl}ethoxy}carbonyl; dnseoc) group a new variation in oligodeoxyribonucleotide synthesis
  作者：Thomas Wagner、Wolfgang Pfleiderer

  DOI：10.1002/hlca.19970800118

  日期：1997.2.10

  (2-dansylethoxy)carbonyl (= 2-[5-(dimethylamino)naphthalen-l-yl]sulfonyl}ethoxy}carbonyl; dnseoc) group was employed for protection of the amino functions of the aglycone residues. The lactam function of 2′-deoxyguanosine was on the one hand unprotected and on the other hand alkylated at O6 of the aglycone with the 2-(4-nitrophenyl)ethyl (npe) and 2-(phenylsulfonyl)ethyl (pse) group, respectively. The syntheses

  （2-丹酰基乙氧基）羰基（＝ 2-[5-（二甲基氨基）萘-1-基]磺酰基}乙氧基}羰基； dnseoc）基团用于保护糖苷配基残基的氨基官能团。2'-脱氧鸟苷的内酰胺功能一方面未受保护，另一方面在O 6处烷基化糖苷配基分别具有2-（4-硝基苯基）乙基（npe）和2-（苯基磺酰基）乙基（pse）的基团。描述了三种常见的2'-脱氧核苷（2'-脱氧胞苷，2'-脱氧腺苷，2'-脱氧鸟苷）的单体结构单元（亚磷酰胺和核苷官能化载体）的合成。正如对三苯甲基化核苷的动力学研究表明，与相应的2-（4-硝基苯基）乙基-（npe）和[2-（4-硝基苯基）乙氧基]羰基（npeoc）-保护的dnseoc基团相比，Dse裂解更不稳定。类似物（参见表2）。这些结果被dnseoc基团在某些寡核苷酸上的快速去保护率所证实。
• Phthaloyl Strategy—A New Approach Towards Oligodeoxyribonucleotide Synthesis
  作者：Markus Beier、Wolfgang Pfleiderer

  DOI：10.1080/07328319708006240

  日期：1997.7

  A new rapid strategy for machine-aided oligodeoxyribonucleotide synthesis has been established utilizing phthaloyl groups for protection of the heterocyclic amino functions within the phosphoramidite approach. A large number of DNA-sequences has been synthesized. Due to high purity and speed of performance this strategy offers an excellent alternative to the common used acyl approach.