4-N-benzoyl-2'-deoxy-5'-O-(tert-butyldiphenylsilyl)cytidine | 139244-40-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-N-benzoyl-2'-deoxy-5'-O-(tert-butyldiphenylsilyl)cytidine
• 英文别名: 5'-O-tert-butyldiphenylsilyl-N⁴-benzoyl-2'-deoxycytidine；N-(1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide；N-Benzoyl-2'-deoxy-5'-O-[(1,1-dimethylethyl)diphenylsilyl]Cytidine；N-[1-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 139244-40-9
• 化学式: C₃₂H₃₅N₃O₅Si
• 分子量: 569.732
• InChiKey: PCGCWUMQXDGYFX-YIKNKFAXSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-N-benzoyl-2'-deoxy-5'-O-(tert-butyldiphenylsilyl)cytidine 在 四丁基氟化铵 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  核苷-O-甲基膦酸酯：修饰寡核苷酸的单体池

  摘要：

  四种天然 2'-脱氧核糖核苷、1-（2-脱氧-β-D-苏式-戊呋喃糖基）胸腺嘧啶、5'-O- 和 2' 的一组独特的 5'-O- 和 3'-O-膦酰基甲基衍生物1-(3-脱氧-β-D-赤型-戊呋喃糖基)胸腺嘧啶和1-(3-脱氧-β-D-苏式-戊呋喃糖基)胸腺嘧啶的-O-膦酰基甲基衍生物已被合成为单体库修饰寡核苷酸的合成。膦酸酯部分用 4-甲氧基-1-氧化-2-吡啶基甲酯基团保护，在偶联步骤中也作为分子内催化剂。

  DOI：

  10.1081/ncn-200033912
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-N-benzoyl-2'-deoxy-5'-O-(tert-butyldiphenylsilyl)cytidine
  参考文献：
  名称：

  [EN] NUCLEOTIDE CLEAVABLE LINKERS AND USES THEREOF
  [FR] LIEURS CLIVABLES NUCLÉOTIDIQUES ET LEURS UTILISATIONS

  摘要：

  在此披露的内容包括化合物、组合物以及它们的使用方法，用于测序核酸。

  公开号：

  WO2020146397A1

文献信息

• [EN] THERMALLY-CLEAVABLE PROTECTING AND LINKER GROUPS<br/>[FR] GROUPES PROTECTEURS ET DE LIAISON THERMIQUEMENT CLIVABLES
  申请人：EVONETIX LTD

  公开号：WO2018189546A1

  公开（公告）日：2018-10-18

  The present invention relates to chemical linkers and protecting groups, compounds and compositions containing the chemical linkers or protecting groups, and intermediates and processes that can be used to prepare them. The chemical linkers and protecting groups are based on pyrrolidine and piperidine activating groups, which undergo intramolecular cyclisation upon heating with release of carbon dioxide, thereby releasing the organic compound from a substrate. In particular, those chemical linkers and protecting groups are useful in the solid phase synthesis of oligonucleotides according to the following representative schemes.

  本发明涉及化学连接剂和保护基团，含有化学连接剂或保护基团的化合物和组合物，以及可用于制备它们的中间体和过程。这些化学连接剂和保护基团基于吡咯烷和哌哆啶活化基团，加热后发生分子内环化，并释放二氧化碳，从而释放有机化合物从底物中。特别是，这些化学连接剂和保护基团在寡核苷酸的固相合成中具有用途，具体方案如下。
• Efficient Synthesis of 2′-Deoxynucleoside 3′-C-Phosphonates: Reactivity of Geminal Hydroxyphosphonate Moiety
  作者：Śárka Králíková、Miloś Buděšínský、Milena Masojídková、Ivan Rosenberg

  DOI：10.1080/15257770008035038

  日期：2000.7

  In this report we present a novel, simple way for the synthesis of 3'-C-phosphonate derivatives of all four basic 2'-deoxynucleosides in both fully protected and deprotected forms. The reactivity of the geminal hydroxy phosphonate moiety located at the 3'-carbon atom of the nucleoside was studied with respect to the use of this type of nucleoside phosphonic acid for the preparation of short oligonucleotides

  在本报告中，我们提出了一种新颖，简单的方法，用于以完全保护和脱保护的形式合成所有四个基本2'-脱氧核苷的3'-C-膦酸酯衍生物。关于使用这种类型的核苷膦酸制备短寡核苷酸，即二核苷单磷酸类似物，研究了位于核苷的3'-碳原子处的双羟基膦酸酯部分的反应性。
• Preparation of Purine 2'-Deoxy-5'-O-phosphonomethylnucleosides and 2'-Deoxy-3'-O-phosphonomethylnucleosides
  作者：Marcela Krečmerová、Hubert Hřebabecký、Milena Masojídková、Antonín Holý

  DOI：10.1135/cccc19930421

  日期：——

  Sodium salt of 2'-deoxy-N⁶-dimethylaminomethylene-3'-O-(tetrahydro-2H-pyran-2-yl)adenosine (VIII) reacted with dibenzyl p-toluenesulfonyloxymethanephosphonate (Ia) to give dibenzyl ester of 2'-deoxy-N⁶-dimethylaminomethylene-5'-O-phosphonomethyl-3'-O-(tetrahydro-2H-pyran-2-yl)adenosine (XI) which after deprotection afforded the final 2'-deoxy-5'-O-phosphonomethyladenosine (XII). 2'-Deoxy-5'-O-hydroxymethanephosphonyladenosine (XIV) and 5'-O-benzyloxymethanephosphonyl-2'-deoxyadenosine (XIII) were isolated as a side product. The preparation of 2'-deoxy-5'-O-phosphonomethylguanosine (XVI) and protection of the starting nucleoside were analogous to those of compound XII. In the 2'-deoxy-3'-O-phosphonomethylnucleosides series, 2'-deoxy-3'-O-phosphonomethylcytidine (XXI) and 2'-deoxy-3'-O-phosphonomethyladenosine (XXVII) were prepared, using N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-2'-deoxycytidine (XVIII) and 5'-O-tert-butyldiphenylsilyl-2'-deoxy-N⁶-dimethylaminomethyleneadenosine (XXIV), respectively, as starting compounds.

  2'-脱氧核苷酸（XII）的制备方法如下：先将2'-脱氧-N6-二甲氨基甲基烯基-3'-O-(四氢-2H-吡喃-2-基)腺苷（VIII）的钠盐与二苄基对甲苯磺酰氧甲基膦酸酯（Ia）反应，得到2'-脱氧-N6-二甲氨基甲基烯基-5'-O-膦酸甲酯-3'-O-(四氢-2H-吡喃-2-基)腺苷的二苄基酯（XI），去保护后得到最终产物2'-脱氧-5'-O-膦酸甲基腺苷（XII）。2'-脱氧-5'-O-羟甲基膦酸酯腺苷（XIV）和5'-O-苄氧甲基膦酸酯-2'-脱氧腺苷（XIII）为副产物。2'-脱氧-5'-O-膦酸甲基鸟苷（XVI）的制备和起始核苷的保护与化合物XII类似。在2'-脱氧-3'-O-膦酸甲基核苷系列中，使用N4-苯甲酰-5'-O-叔丁基二苯基硅基-2'-脱氧胞苷（XXI）和5'-O-叔丁基二苯基硅基-2'-脱氧-N6-二甲氨基甲基烯基腺苷（XXIV）作为起始化合物，制备了2'-脱氧-3'-O-膦酸甲基胞苷（XXI）和2'-脱氧-3'-O-膦酸甲基腺苷（XXVII）。
• Krecmerova, Marcela; Hrebabecky, Hubert; Holy, Antonin, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 10, p. 2521 - 2536
  作者：Krecmerova, Marcela、Hrebabecky, Hubert、Holy, Antonin

  DOI：——

  日期：——
• Solid-phase synthesis of branched RNA and branched DNA/RNA chimeras
  作者：Morten Grøtli、Ramon Eritja、Brian Sproat

  DOI：10.1016/s0040-4020(97)00731-x

  日期：1997.8

  An effective method for synthesising branched oligonucleotides on solid phase in the 5' to 3' direction has been developed. Special branch-point monomers enable the synthesis of branched oligonucleotides which can have sequences of different length and base composition attached to the 2'-and 3'-hydroxyl groups of the branch point ribonucleoside. The branched oligonucleotides are assembled on commercial DNA synthesisers, the crude products are readily purified by reversed phase HPLC and the fully deprotected products are conveniently analysed by mass spectrometry. (C) 1997 Elsevier Science Ltd.