2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-phthaloyladenosine | 84780-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-phthaloyladenosine
• 英文别名: 2-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]purin-6-yl]isoindole-1,3-dione
• CAS: 84780-16-5
• 化学式: C₃₉H₃₃N₅O₇
• 分子量: 683.72
• InChiKey: OAXTVJSAPCWDBF-WIHCDAFUSA-N

物化性质

• 沸点：
  881.2±75.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  51
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-phthaloyladenosine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.03h， 生成 5-O-(4,4-二甲氧基三苯甲游基)-2-脱氧腺苷酸
  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：

  2'-脱氧腺苷 在 吡啶 、 三甲基氯硅烷 、 水 作用下， 生成 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-phthaloyladenosine
  参考文献：
  名称：

  Phthaloyl Strategy—A New Approach Towards Oligodeoxyribonucleotide Synthesis

  摘要：

  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.

  DOI：

  10.1080/07328319708006240

文献信息

• Phthaloyl group : a new amino protecting group of deoxyadenosine in oligonucleotide synthesis
  作者：Akiko Kume、Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1016/s0040-4039(00)85601-4

  日期：1982.1

  A phthaloyl group has been introduced into the N6-amino group of deoxyadenosine silylation followed by acylation. The phthaloyl group resulted in remarkable retarding effects on depurination, while it could be removed under milder conditions than the benzoyl group. Thus, a tetradeoxyadenylate has been successfully synthesized in high yield.

  已将邻苯二甲酰基引入到脱氧腺苷甲硅烷基化的N 6-氨基中，然后进行酰化。邻苯二甲酰基对脱嘌呤具有显着的阻滞作用，而在比苯甲酰基更温和的条件下可以除去。因此，已经成功地高产率地合成了四脱氧腺苷酸酯。