5'-O-TIPS-2'-deoxyadenosine | 1278473-86-1

• 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: 5'-O-TIPS-2'-deoxyadenosine
• CAS: 1278473-86-1
• 化学式: C₁₉H₃₃N₅O₃Si
• 分子量: 407.588
• InChiKey: QOSUPETYZJGLCS-ARFHVFGLSA-N

物化性质

• 沸点：
  554.0±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  5'-O-TIPS-2'-deoxyadenosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以98.36 %的产率得到2'-脱氧腺苷
  参考文献：
  名称：

  一种羟甲基的保护及脱保护方法

  摘要：

  本发明公开了一种羟甲基的保护及脱保护方法，包括保护过程和脱保护过程：所述保护过程为：将含羟甲基化合物和三异丙基氯硅烷通过缩合反应，在羟甲基上修饰三异丙基硅烷基团；所述脱保护过程为：修饰三异丙基硅烷基团的羟甲基化合物在四丁基氟化铵作用下进行脱保护基反应，得到含羟甲基化合物。该方法利用具有氟敏感性的三异丙基氯硅烷作为羟甲基保护基，具有高选择性和高结合率的特点，且极易在四丁基氟化铵作用下水解脱除，脱除效率高，整个保护和脱保护过程简单，条件温和，反应速率快，有利于扩大生产应用。

  公开号：

  CN117466963A
• 作为产物：
  描述：

  三异丙基氯硅烷 、 1-(6-amino-purin-9-yl)-1,2-dideoxy-pentofuranose 在 咪唑 作用下， 以 氘代二甲亚砜 为溶剂， 以89.4 %的产率得到5'-O-TIPS-2'-deoxyadenosine
  参考文献：
  名称：

  一种羟甲基的保护及脱保护方法

  摘要：

  本发明公开了一种羟甲基的保护及脱保护方法，包括保护过程和脱保护过程：所述保护过程为：将含羟甲基化合物和三异丙基氯硅烷通过缩合反应，在羟甲基上修饰三异丙基硅烷基团；所述脱保护过程为：修饰三异丙基硅烷基团的羟甲基化合物在四丁基氟化铵作用下进行脱保护基反应，得到含羟甲基化合物。该方法利用具有氟敏感性的三异丙基氯硅烷作为羟甲基保护基，具有高选择性和高结合率的特点，且极易在四丁基氟化铵作用下水解脱除，脱除效率高，整个保护和脱保护过程简单，条件温和，反应速率快，有利于扩大生产应用。

  公开号：

  CN117466963A

文献信息

• Syntheses of Aliphatic Polycarbonates from 2′-Deoxyribonucleosides
  作者：Masato Suzuki、Toyokazu Sekido、Shin-ichi Matsuoka、Koji Takagi

  DOI：10.1021/bm101328j

  日期：2011.5.9

  Poly(2'-deoxyadenosine) and poly(thymidine) constructed of carbonate linkages were synthesized by poly-condensation between silyl ether and carbonylimidazolide at the 3'- and 5'-positions of the 2'-deoxyribonucleoside monomers. The N-benzoyl-2'-deoxyadenosine monomer afforded the corresponding polycarbonate together with the cyclic oligomers. However, the deprotection of the N-benzoyl group resulted in the scission of the polymer main chain. Thus, the N-unprotected 2'-deoxyadenosine monomers were examined for polycondensation. However, there was involved the undesired reaction between the adenine amino group and the carbonylimidazolide to form the carbamate linkage. In order to exclude this unfavorable reaction, dynamic protection was employed. Strong hydrogen bonding was used in place of the usual covalent bonding for reducing the nucleophilicity of the adenine amino group. Herein, 3',5'-O-diacylthymidines that form the complementary hydrogen bonding with the adenine amino group were added to the polymerization system of the N-unprotected 2'-deoxyadenosine monomer. Consequently, although the oligomers (M-n = 1000-1500) were produced, the contents of the carbamate group were greatly reduced. The dynamic protection reagents were easily and quantitatively recovered as the MeOH soluble parts from the polymerization mixtures. In the polycondensation of the thymidine monomer, there tended to be involved another unfavorable reaction of carbonate exchange, which consequently formed the irregular carbonate linkages at not only the but also the 3'-3' and positions. Employing the well-designed monomer suppressed the carbonate exchange reaction to produce poly(thymidine) with the almost regular 3'-5'carbonate linkages.