3',5'-bis-O-trimethylsilyl-2'-deoxyguanosine | 129184-64-1

• 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: 3',5'-bis-O-trimethylsilyl-2'-deoxyguanosine
• 英文别名: 2-amino-9-[(2R,4S,5R)-4-trimethylsilyloxy-5-(trimethylsilyloxymethyl)oxolan-2-yl]-3H-purin-6-one
• CAS: 129184-64-1
• 化学式: C₁₆H₂₉N₅O₄Si₂
• 分子量: 411.608
• InChiKey: MWHWALNMLPOHPH-QJPTWQEYSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  117.28
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3',5'-bis-O-trimethylsilyl-2'-deoxyguanosine 在 吡啶 、 水 作用下， 反应 7.0h， 生成 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-[(2-nitrophenyl)sulfanylamino]-1H-purin-6-one
  参考文献：
  名称：

  Awasthi, S. K.; Khanna, V.; Watal, G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 6, p. 326 - 329

  摘要：

  DOI：
• 作为产物：
  描述：

  3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 在 吡啶 、 六甲基磷酰三胺 、 叔丁基氯化镁 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 5.75h， 生成 3',5'-bis-O-trimethylsilyl-2'-deoxyguanosine
  参考文献：
  名称：

  Photocleavable Protecting Groups as Nucleobase Protections Allowed the Solid-Phase Synthesis of Base-Sensitive SATE-Prooligonucleotides

  摘要：

  The first synthesis of oligodeoxynucleotide heteropolymers carrying base-sensitive S-pivaloylthioethyl (t-Bu-SATE) phosphotriester linkages has been performed. It is based on the use of 6-nitroveratryloxycarbonyl (NVOC) and 2,2'-bis(2-nitrophenyl)ethoxycarbonyl (diNPEOC) groups as nucleobase protections in combination with photolysis deprotection. The synthesis was realized using the phosphoramidite approach on solid support bearing a 1-(o-nitrophenyl)-1,3-propanediol linker. The removal of the protecting groups and the cleavage of the oligonucleotides from the solid support were accomplished in a single photolysis procedure upon UV irradiation at wavelengths >300 nn. Faster deprotection rates were observed for diNPEOC-protected nucleosides and oligomers than with NVOC-protected ones. The synthesis of pentanucleoside t-Bu-SATE-phosphotriesters d((5')TpCpCpCpTp(3')), d((5')TpApApApAp(3')), and d((5')TpGpGpGpTp(3')) and of dodecanucleoside t-Bu-SATE-phosphotriesters and -phosphorothioate d((5')ApCpApCpCpCpApApTpTpCpTp(3')) and d((5')ApGpApApTpTpGpGpGpTpGpTp(3')) demonstrated the efficiency of the method.

  DOI：

  10.1021/jo990479h

文献信息

• Nucleotides, Part LXVII, The 2-Cyanoethyl and (2-Cyanoethoxy)carbonyl Group for Base Protection in Nucleoside and Nucleotide Chemistry
  作者：Claudia Merk、Tilman Reiner、Evgeny Kvasyuk、Wolfgang Pfleiderer

  DOI：10.1002/1522-2675(20001220)83:12<3198::aid-hlca3198>3.0.co;2-q

  日期：2000.12.20

  The amino functions of the common 2′-deoxyribo- and ribonucleosides were blocked by the (2-cyanoethoxy)carbonyl group on treatment with 2-cyanoethyl carbonochloridate (5) or 1-[(2-cyanoethoxy)carbonyl]-3-methyl-1H-imidazolium chloride (6) leading to 7, 18, 8, 19, 9, and 20. In 2′-deoxyguanosine, the amide group was additionally blocked at the O6 position by the 2-cyanoethyl (27) and 2-(4-nitrophenyl)ethyl

  在用 2-氰基乙基碳氯酸酯 (5) 或 1-[(2-氰基乙氧基)羰基]-3-甲基-处理时，常见的 2'-脱氧核糖和核糖核苷的氨基官能团被 (2-氰基乙氧基)羰基封闭。 1H-咪唑氯化物 (6) 产生 7, 18, 8, 19, 9 和 20。在 2'-脱氧鸟苷中，酰胺基团在 O6 位被 2-氰乙基 (27) 和 2-( 4-硝基苯基)乙基(31, 32)。关于通过 β-消除裂解 ce/ceoc 和 npe/npeoc 基团的比较动力学研究揭示了有关核碱基不同位点的各种封闭基团的容易性和顺序脱保护的有价值的信息。
• A new protected acyl protecting group for exocyclic amino functions of nucleobases
  作者：C.M. Dreef-Tromp、P. Hoogerhout、G.A. van der Marel、J.H. van Boom

  DOI：10.1016/s0040-4039(00)94573-8

  日期：1990.1

  reacts with the per-O-trimethylsilylated d-nucleosides C,G and A to give, after removal of the Si(Me)3 groups and 5'-O-protection with 4,4'-dimethoxytrityl chloride (DMT-Cl), the corresponding N-SiOMB-5'-O-DMT derivates, the SiOMB groups of which can easily be removed by fluoride ion. The SiOMB protected nucleosides proved to be suitable building units for the preparation of DNA fragments in solution and

  2-（叔丁基二苯基甲硅烷氧基甲基）苯甲酰氯（SiOMB-Cl）与过-O-三甲基甲硅烷基化的d-核苷C，G和A反应，除去Si（Me）3基团并进行5'-O-保护后得到含有4,4'-二甲氧基三苯甲基氯（DMT-Cl）的相应N-SiOMB-5'-O-DMT衍生物，其SiOMB基很容易被氟离子除去。SiOMB保护的核苷被证明是在溶液中和在固体支持物上制备DNA片段的合适构建单元。
• 2-(Azidomethyl)benzoyl as a new protecting group in nucleosides
  作者：Takeshi Wada、Akihiro Ohkubo、Akira Mochizuki、Mitsuo Sekine

  DOI：10.1016/s0040-4039(00)02183-3

  日期：2001.2

  A new protecting group, 2-(azidomethyl)benzoyl (AZMB), which can be easily removed by treatment with MePPh2 in dioxane–H2O or reduction with HCOONH4–Pd/C in dioxane–MeOH, was developed for protection of the hydroxy and amino functions of deoxyribonucleosides.

  开发了一种新的保护基2-（叠氮甲基）苯甲酰基（AZMB），可以通过在二恶烷-H 2 O中用MePPh 2处理或在二恶烷-MeOH中用HCOONH 4 -Pd / C还原而轻松除去。脱氧核糖核苷的羟基和氨基官能团。
• Synthesis of Guanosine and Deoxyguanosine Phosphoramidites with Cross-Linkable Thioalkyl Tethers for Direct Incorporation into RNA and DNA
  作者：Xiaorong Hou、Gang Wang、Barbara L. Gaffney、Roger A. Jones

  DOI：10.1080/15257770903368385

  日期：2009.12.7

  describe the synthesis of protected phosphoramidites of deoxyriboguanosine and guanosine derivatives containing a thiopropyl tether at the guanine N2 (7a,b) for site-specific crosslinking from the minor groove of either DNA or RNA to a thiol of a protein or another nucleic acid. The thiol is initially protected as a tert-butyl disulfide that is stable during oligonucleotide synthesis. While the completed

  我们描述了脱氧核糖鸟苷和鸟苷衍生物的受保护亚磷酰胺的合成，在鸟嘌呤 N2 ( 7a , b ) 处含有硫丙基系链，用于从 DNA 或 RNA 的小沟与蛋白质或另一种核酸的硫醇进行位点特异性交联。硫醇最初被保护为叔丁基二硫醚，其在寡核苷酸合成过程中是稳定的。当完成的寡核苷酸仍附着在载体上时，或在纯化后，叔丁基硫醇可以很容易地被去除或被硫乙胺或5-硫代-2-硝基苯甲酸取代，它们具有更有利的交联速率。
• Introduction of the 4,4′4′-tris(benzoyloxy)trityl group into the exo amino groups of deoxyribonucleosides and its properties
  作者：Mitsuo Sekine、Narihiro Masuda、Tsujiaki Hata

  DOI：10.1016/s0040-4020(01)91344-4

  日期：1985.1

  The 4,4′,4′-tris(benzoyloxy)trityl (TBTr) group was introduced into the amino groups of the common deoxyribonucleosides by means of the transient protection using the trimethylsilyl group. The TBTr group introduced onto the N6 -amino group of deoxyadenosine was found to have considerable retarding effects on the depurination when treated with acids.

  通过使用三甲基甲硅烷基的瞬时保护，将4,4'，4'-三（苯甲酰氧基）三苯甲基（TBTr）基团引入常见的脱氧核糖核苷的氨基中。发现引入到脱氧腺苷的N 6-氨基上的TBTr基团在用酸处理时对脱嘌呤具有相当大的阻滞作用。