6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thioguanosine | 1225490-73-2

• 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: 6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thioguanosine
• 英文别名: 2-ethylhexyl 3-[2-amino-9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-yl]sulfanylpropanoate
• CAS: 1225490-73-2
• 化学式: C₃₃H₆₁N₅O₅SSi₂
• 分子量: 696.115
• InChiKey: UMJPQQGMGQZEOT-ZIIKXKDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.35
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thioguanosine 、 苯氧乙酰氯 在 吡啶 、 1-羟基苯并三唑 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以84%的产率得到6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-2-N-phenoxyacetyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thioguanosine
  参考文献：
  名称：

  A New Odorless Procedure for the Synthesis of 2′-Deoxy-6-Thioguanosine and Its Incorporation into Oligodeoxynucleotides

  摘要：

  6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl)}-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thiogua nosine (2) was synthesized in high yield from the corresponding 6-O-mesitylenesulfonyl derivative by the reaction with 2-ethylhexyl 3-mercapto-propionate. The phosphoramidite precursor derived from 2 was successfully applied to an automated DNA synthesizer to produce 2'-deoxy-6-thioguanosine containing ODN. The results showed that 2-ethylhexyl 3-mercaptopropionate is useful as an odor less reagent and also as an S-protecting group of 2'-deoxy-6-thioguanosine.

  DOI：

  10.1080/15257770903155576
• 作为产物：
  描述：

  3-巯基丙酸-2-乙己酯 、 3',5'-bis-O-(tert-butyldimethylsilyl)-O⁶-[(2,4,6-trimethylphenyl)sulfonyl]-2'-deoxyguanosine 以 N-甲基吡咯烷酮 为溶剂， 以1.34 g的产率得到6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thioguanosine
  参考文献：
  名称：

  A New Odorless Procedure for the Synthesis of 2′-Deoxy-6-Thioguanosine and Its Incorporation into Oligodeoxynucleotides

  摘要：

  6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl)}-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thiogua nosine (2) was synthesized in high yield from the corresponding 6-O-mesitylenesulfonyl derivative by the reaction with 2-ethylhexyl 3-mercapto-propionate. The phosphoramidite precursor derived from 2 was successfully applied to an automated DNA synthesizer to produce 2'-deoxy-6-thioguanosine containing ODN. The results showed that 2-ethylhexyl 3-mercaptopropionate is useful as an odor less reagent and also as an S-protecting group of 2'-deoxy-6-thioguanosine.

  DOI：

  10.1080/15257770903155576

文献信息

• A New Odorless Procedure for the Synthesis of 2′-Deoxy-6-Thioguanosine and Its Incorporation into Oligodeoxynucleotides
  作者：Kazumitsu Onizuka、Yosuke Taniguchi、Shigeki Sasaki

  DOI：10.1080/15257770903155576

  日期：2009.9.11

  6-S-2-[(2-ethylhexyl)oxycarbonyl]ethyl)}-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thiogua nosine (2) was synthesized in high yield from the corresponding 6-O-mesitylenesulfonyl derivative by the reaction with 2-ethylhexyl 3-mercapto-propionate. The phosphoramidite precursor derived from 2 was successfully applied to an automated DNA synthesizer to produce 2'-deoxy-6-thioguanosine containing ODN. The results showed that 2-ethylhexyl 3-mercaptopropionate is useful as an odor less reagent and also as an S-protecting group of 2'-deoxy-6-thioguanosine.