6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-5'-O-(4,4'-dimethoxytrityl)-2-N-phenoxyacetyl-2'-deoxy-6-thioguanosine | 1242460-59-8

• 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: 6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-5'-O-(4,4'-dimethoxytrityl)-2-N-phenoxyacetyl-2'-deoxy-6-thioguanosine
• CAS: 1242460-59-8
• 化学式: C₅₀H₅₇N₅O₉S
• 分子量: 904.097
• InChiKey: LEJIAEPMFDVIAZ-DMIGAJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.76
• 重原子数：
  65.0
• 可旋转键数：
  23.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  165.38
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-5'-O-(4,4'-dimethoxytrityl)-2-N-phenoxyacetyl-2'-deoxy-6-thioguanosine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.42h， 以77%的产率得到6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-5'-O-(4,4'-dimethoxytrityl)-2-N-phenoxyacetyl-2'-deoxy-6-thioguanosine-3'-O-(2-cyanoethyl)(N,N-diisopropyl)phosphoramidite
  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：

  6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-2-N-phenoxyacetyl-2'-deoxy-6-thioguanosine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 1.0h， 以94%的产率得到6-S-{2-[(2-ethylhexyl)oxycarbonyl]ethyl}-5'-O-(4,4'-dimethoxytrityl)-2-N-phenoxyacetyl-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