6-O-tosyl-2',3',5'-tri-O-tert-butyldimethylsilyl-guanosine | 161803-87-8

• 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-O-tosyl-2',3',5'-tri-O-tert-butyldimethylsilyl-guanosine
• 英文别名: [2-amino-9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-yl] 4-methylbenzenesulfonate
• CAS: 161803-87-8
• 化学式: C₃₅H₆₁N₅O₇SSi₃
• 分子量: 780.221
• InChiKey: RELUBRREMOMAGV-QWOIFIOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-tosyl-2',3',5'-tri-O-tert-butyldimethylsilyl-guanosine 在 四(三苯基膦)钯 、 camphor-10-sulfonic acid 、 lithium chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 4-[2-[2-amino-9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-yl]ethylamino]-1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]pyrimidin-2-one
  参考文献：
  名称：

  2-Aminopurine derivatives with C6-substituted olefin as novel cross-linking agents and the synthesis of the corresponding β-phosphoramidite precursors

  摘要：

  The 6-vinylated 2-aminopurine nucleoside (1), which was prepared by the Pd(0)-catalyzed cross-coupling reaction using guanosine 6-O-tosylate and vinyl-tributylstannane, has been demonstrated as a potential cross-linking agent. However, attempts for its incorporation into oligonucleotides were unsuccessful because of the high reactivity toward nucleophiles. In this study, new 2'-deoxy nucleoside derivatives with 6-(2-substituted vinyl)-2-aminopurine were designed to diminish the reactivity of the vinyl group. These new nucleosides have been shown to maintain reactivity toward potent nucleophiles such as butylamine and thiols, suggesting that they would form cross-linking with the target nucleobase due to the proximity within the sense-antisense duplex. Thus, the corresponding beta-phosphoramidite precursors were successfully prepared, and were applied to an automated oligonucletotide synthesizer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00069-0
• 作为产物：
  描述：

  鸟苷 在 咪唑 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 6-O-tosyl-2',3',5'-tri-O-tert-butyldimethylsilyl-guanosine
  参考文献：
  名称：

  2-Aminopurine derivatives with C6-substituted olefin as novel cross-linking agents and the synthesis of the corresponding β-phosphoramidite precursors

  摘要：

  The 6-vinylated 2-aminopurine nucleoside (1), which was prepared by the Pd(0)-catalyzed cross-coupling reaction using guanosine 6-O-tosylate and vinyl-tributylstannane, has been demonstrated as a potential cross-linking agent. However, attempts for its incorporation into oligonucleotides were unsuccessful because of the high reactivity toward nucleophiles. In this study, new 2'-deoxy nucleoside derivatives with 6-(2-substituted vinyl)-2-aminopurine were designed to diminish the reactivity of the vinyl group. These new nucleosides have been shown to maintain reactivity toward potent nucleophiles such as butylamine and thiols, suggesting that they would form cross-linking with the target nucleobase due to the proximity within the sense-antisense duplex. Thus, the corresponding beta-phosphoramidite precursors were successfully prepared, and were applied to an automated oligonucletotide synthesizer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00069-0

文献信息

• NOVEL ARTIFICIAL FLUORESCENT BASES
  申请人：Riken

  公开号：EP2487180B1

  公开（公告）日：2014-12-03
• 2-Aminopurine derivatives with C6-substituted olefin as novel cross-linking agents and the synthesis of the corresponding β-phosphoramidite precursors
  作者：Fumi Nagatsugi、Kengo Uemura、Shouji Nakashima、Minoru Maeda、Shigeki Sasaki

  DOI：10.1016/s0040-4020(97)00069-0

  日期：1997.3

  The 6-vinylated 2-aminopurine nucleoside (1), which was prepared by the Pd(0)-catalyzed cross-coupling reaction using guanosine 6-O-tosylate and vinyl-tributylstannane, has been demonstrated as a potential cross-linking agent. However, attempts for its incorporation into oligonucleotides were unsuccessful because of the high reactivity toward nucleophiles. In this study, new 2'-deoxy nucleoside derivatives with 6-(2-substituted vinyl)-2-aminopurine were designed to diminish the reactivity of the vinyl group. These new nucleosides have been shown to maintain reactivity toward potent nucleophiles such as butylamine and thiols, suggesting that they would form cross-linking with the target nucleobase due to the proximity within the sense-antisense duplex. Thus, the corresponding beta-phosphoramidite precursors were successfully prepared, and were applied to an automated oligonucletotide synthesizer. (C) 1997 Elsevier Science Ltd.