(6aR,8R,9R,9aS)-8-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol | 81243-94-9

• 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: (6aR,8R,9R,9aS)-8-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol
• CAS: 81243-94-9
• 化学式: C₄₂H₅₅N₅O₆Si₂
• 分子量: 782.1
• InChiKey: LTLFVMAOCGRIFO-LSZAAVILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.45
• 重原子数：
  55
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (6aR,8R,9R,9aS)-8-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol 在 potassium fluoride 、 2,4-二磺酰氯基均三甲苯 、 四乙基溴化铵 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 吡啶 、 水 、 乙腈 为溶剂， 反应 7.0h， 生成 Dithiophosphoric acid O-[(2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl] ester S,S'-diphenyl ester
  参考文献：
  名称：

  利用S，S-二苯基n-单甲氧基三苯甲基三核糖核苷3'-phosphodiodithioates合成寡核糖核苷酸

  摘要：

  经过5步或6步反应，完全保护的核糖核苷酸单元（6a–d）的总产率为42–62％。将二甲氧基三苯甲基，单甲氧基三苯甲基，四氢吡喃-2-基和苯硫基分别引入到5'-OH，外-氨基，2'-OH和3'-磷酰基官能团上。通过用三氟乙酸或次膦酸-三乙胺处理，将单元转化为OH或磷酸二酯组分。借助于均三甲苯二甲磺酰氯3-硝基-1,2,4-三唑适当地偶联两种组分，以高收率得到二聚体。该方法已成功应用于GpUpApUpUpApApUpAp的合成，即溴化花叶病毒4号RNA细丝的5'端碱基序列。

  DOI：

  10.1016/0040-4020(84)85114-5
• 作为产物：
  描述：

  腺苷 在 4-二甲氨基吡啶 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (6aR,8R,9R,9aS)-8-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol
  参考文献：
  名称：

  新型预制全保护核糖核苷酸单体单元作为快速寡核苷酸合成中有用的合成中间体

  摘要：

  寡核糖核苷酸合成是通过使用新构建的完全受保护的核糖核苷酸单元 S,S-二苯基 5'-O-二甲氧基三苯甲基-2'-O-四氢吡喃基-N-单甲氧基三苯甲基核苷 3'-二硫代磷酸酯 7 完成的。发现这些单元是有用的合成用于快速寡核糖核苷酸合成的中间体。

  DOI：

  10.1246/cl.1982.15

文献信息

• Chemical Synthesis of a 5‘-Terminal TMG-Capped Triribonucleotide m₃^2,2,7G⁵^‘pppAmpUmpA of U1 RNA
  作者：Mitsuo Sekine、Michinori Kadokura、Takahiko Satoh、Kohji Seio、Takeshi Wada、Utz Fischer、Vicki Sumpter、Reinhard Lührmann

  DOI：10.1021/jo952263v

  日期：1996.1.1

  The 5'-terminal TMG-capped triribonucleotide, m(3)(2,2,7)G(5')pppAmpUmpA, has been synthesized by condensation of an appropriately protected triribonucleotide derivative of ppAmpUmpA with a new TMG-capping reagent. During this total synthesis, it was found that the regioselective 2'-O-methylation of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N-(4-monomethoxytrityl)adenosine was achieved by use of MeI/Ag2O without affecting the base moiety. A new route to 2-N,2-N-dimethylguanosine from guanosine via a three-step reaction has also been developed by reductive methylation using paraformaldehyde and sodium cyanoborohydride. These key intermediates were used as starting materials for the construction of a fully protected derivative of pAmpUmpA and a TMG-capping reagent of Im-pm(3)(2,2,7)G. The target TMG-capped tetramer, m(3)(2,2,7)G(5')pppAmpUmpA, was synthesized by condensation of a partially protected triribonucleotide 5'-terminal diphosphate species, pp(AMMTr)mpUmpA, with Im-pm(3)(2,2,7)G followed by treatment with 80% acetic acid. The structure of m(3)(2,2,7)G(5')pppAmpUmpA was characterized by H-1 and P-31 NMR spectroscopy as well as enzymatic assay using snake venom phosphodiesterase, calf intestinal phosphatase, and nuclease P1.
• NEW TYPE OF PREFABRICATED FULLY PROTECTED RIBONUCLEOTIDE MONOMER UNITS AS USEFUL SYNTHETIC INTERMEDIATES IN RAPID OLIGORIBONUCLEOTIDE SYNTHESIS
  作者：Sinkichi Honda、Kazunori Terada、Yoshinobu Sato、Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1246/cl.1982.15

  日期：1982.1.5

  Oligoribonucleotide synthesis has been done by employing newly constructed fully protected ribonucleotide units, S,S-diphenyl 5′-O-dimethoxytrityl-2′-O-tetrahydropyranyl-N-monomethoxytritylnucleoside 3′-phosphorodithioates 7. The units were found to be useful synthetic intermediates for rapid oligoribonucleotide synthesis.

  寡核糖核苷酸合成是通过使用新构建的完全受保护的核糖核苷酸单元 S,S-二苯基 5'-O-二甲氧基三苯甲基-2'-O-四氢吡喃基-N-单甲氧基三苯甲基核苷 3'-二硫代磷酸酯 7 完成的。发现这些单元是有用的合成用于快速寡核糖核苷酸合成的中间体。
• Synthesis of oligoribonucleotides by use of S,S-diphenyl n-monomethoxytrityl ribonucleoside 3'-phosphorodithioates
  作者：Shinkichi Honda、Ken-ichi Urakami、Kohji Koura、Kazunori Terada、Yoshinobu Sato、Kyoko Kohno、Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1016/0040-4020(84)85114-5

  日期：1984.1

  2'-OH, and 3'-phosphoryl functions, respectively. The units were converted to the OH or phosphodiester components by treatment with trifluoroacetic acid or with phosphinic acid-triethylamine. Both the components were appropriately coupled by means of mesitylenedisulphonyl chloride 3-nitro-1,2,4-triazole to give dimers in high yields. This method was successfully applied to the synthesis of GpUpApUpUpApApUpAp

  经过5步或6步反应，完全保护的核糖核苷酸单元（6a–d）的总产率为42–62％。将二甲氧基三苯甲基，单甲氧基三苯甲基，四氢吡喃-2-基和苯硫基分别引入到5'-OH，外-氨基，2'-OH和3'-磷酰基官能团上。通过用三氟乙酸或次膦酸-三乙胺处理，将单元转化为OH或磷酸二酯组分。借助于均三甲苯二甲磺酰氯3-硝基-1,2,4-三唑适当地偶联两种组分，以高收率得到二聚体。该方法已成功应用于GpUpApUpUpApApUpAp的合成，即溴化花叶病毒4号RNA细丝的5'端碱基序列。