(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl acetate | 17182-39-7

• 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: (2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl acetate
• 英文别名: N⁴-benzoyl-3'-O-acetyldeoxycytidine；N-benzoyl-3'-O-acetyldeoxycytidine；O^3'-acetyl-N⁴-benzoyl-2'-deoxy-cytidine；[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 17182-39-7
• 化学式: C₁₈H₁₉N₃O₆
• 分子量: 373.365
• InChiKey: YHQCWFGKRPKMDG-SQWLQELKSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl acetate 在 吡啶 、 二氯乙酸 、 2,4,6-triisopropylbenzenesulfonyl tetrazolide 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 49.05h， 生成
  参考文献：
  名称：

  Recognition and Inhibition of HIV Integrase by Novel Dinucleotides

  摘要：

  HIV integrase is involved in the integration of viral DNA into chromosomal DNA, a biological process that occurs by a sequence involving HIV DNA splicing and subsequent integration steps. in the quest for small nucleotide systems with nuclease stability of the internucleotide phosphate bond and critical structural features for recognition and inhibition of HIV-1 integrase, we have discovered novel, nuclease-resistant dinucleotides with defined base sequences that are inhibitors of this key viral enzyme. Synthetic methodologies utilized for the syntheses of the novel dinucleotides include an excellent new phosphorylating agent.

  DOI：

  10.1021/ja992528d
• 作为产物：
  描述：

  Acetic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 生成 (2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  三唑基13α-雌激素-核苷生物共轭物的合成及生物学评价。

  摘要：

  通过应用铜催化的炔-叠氮化物点击反应（CuAAC）合成了13α-雌酮的2'-脱氧核苷共轭物。为了引入叠氮基，选择了核苷的5'-位和13α-雌酮的3-羟基上的炔丙基醚官能团。当核苷的3'-羟基被乙酰基保护并且5'-羟基通过甲苯磺酰叠氮化物交换法进行修饰时，我们的手中获得了最佳收率。受保护的5'-叠氮核苷和甾类炔烃之间单击反应的常用条件通过使用1.5当量的Cu（I）催化剂进行了轻微修饰。所有制备的缀合物均通过MTT分析法在体外评估，其针对一组人类粘附细胞系（HeLa，通过体外放射性底物孵育研究了MCF-7和A2780）以及新缀合物对人17β-羟基类固醇脱氢酶1（17β-HSD1）的潜在抑制活性。一些受保护的缀合物对一组人类粘附癌细胞系表现出中等的抗增殖特性（受保护的胞苷缀合物被证明是最有效的，IC50值为9μM）。胸苷偶联物显示出相当大的17β-HSD1抑制活性（IC50 = 19μM）。一些

  DOI：

  10.3390/molecules21091212

文献信息

• Synthesis of deoxyribotetranucleotides by the cyclic enediol phosphorylation method
  作者：Fausto Ramirez、Terrence E. Gavin、Sukhendu B. Mandal、Shripad V. Kelkar、James F. Marecek

  DOI：10.1016/s0040-4020(01)91932-5

  日期：——

  Full experimental details are given for the application of the di(1,2-dimethylethenylene)pyrophosphate method of phosphodiester synthesis to the conversion of deoxyribonucleosides into deoxyribodinucleotides in the dG, dA, dC and dT families. N-(1,2-dimethylethenylenedioxyphosphoryl) imidazole is superior to the corresponding pyrophosphate as a reagent for the conversion of deoxyribodinucleotides into

  给出了磷酸二酯合成的二（1,2-二甲基亚乙基亚乙基）焦磷酸盐方法在dG，dA，dC和dT家族中将脱氧核糖核苷转化为脱氧核糖二核苷酸的完整实验细节。作为用于将脱氧核糖二核苷酸转化为脱氧核糖四核苷酸的试剂，N-（1,2-二甲基亚乙二基二氧基磷酰基）咪唑优于相应的焦磷酸盐。
• [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。
• A new method for the phosphorylation of nucleosides
  作者：Michael Taktakishvili、Vasu Nair

  DOI：10.1016/s0040-4039(00)01251-x

  日期：2000.9

  te (1), was developed for the phosphorylation of primary and secondary alcohols of nucleosides. In the many examples studied, yields in the phosphorylation step were excellent (∼80 to 95%). There is potential for wide applicability of this procedure, not only in nucleoside and nucleotide chemistry, but also in the phosphorylation of biomolecules such as carbohydrates and amino acids.

  开发了一种新的磷酸化试剂2- O-（4,4'-二甲氧基三苯甲基）乙基磺酰lethan-2'-基磷酸酯（1），用于磷酸化核苷的伯醇和仲醇。在许多研究的实例中，磷酸化步骤的收率非常好（约80％至95％）。该方法不仅在核苷和核苷酸化学中，而且在诸如碳水化合物和氨基酸的生物分子的磷酸化中都有广泛的应用潜力。
• Synthesis of 1′#,2′,3′,4′#,5′,5″-2H6-β-D-ribonucleosides and 1′#, 2′,2″,3′,4′#,5′,5″-2H7-β-D-2′-deoxyribonucleosides for selective suppression of proton resonances in partially-deuterated oligo-DNA, oligo-RNA and in 2,5A core (1H-NMR window)
  作者：András Földesi、Frans Peder R. Nilson、Corine Glemarec、Carlo Gioeli、Jyoti Chattopadhyaya

  DOI：10.1016/s0040-4020(01)82001-9

  日期：1992.1

  1′#,2′,3′,4′#,5′,5″-2H6-ribonucleosides 13 – 16 were converted in high yields to the corresponding 1′#,2′,2″,3′,4′#,5′,5″-2H7-2′-deoxynucleosides 41 – 44 in the following manner: 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl (TPDS))-1′#,2′,3′,4#′,5′,5″-2H6-nucleosides 29 – 32 were converted to the corresponding 2′-O-phenoxythiocarbonyl derivatives 33 – 36, which were deoxygenated by tri-n-butyltin

  阮内镍-2 H 2 O在甲基α/β-D-呋喃核糖苷[α/β= 〜3：10] 1的差向异构体混合物上的交换反应产生了甲基1 ＃，2,3,4 ＃，5,5'- 2 H 6 -α/β-呋喃核糖苷2 [在C2，C3，C5 / 5'处为97原子％2 H；C 4（C4 ＃）〜85原子％2 H ；在C1（C1 ＃）]处约20个原子％2 H，以60 – 80％的产率获得，同时还得到了差向异构的木糖和阿拉伯糖副产物。在干燥的吡啶中将粗产物2甲苯磺酸化，并在硅胶柱上小心分离，得到纯的1-O-甲基-2,3,5-三-O-（4-甲苯甲酰基）-α/β-D-1＃，2,3,4 ＃，5,5'- 2 H 6-核呋喃糖苷4（48％）。4转化为1-O-乙酰基-2,3,5-三-O-甲苯甲酰基-α/β-D-1 ＃，2,3,4 ＃，5,5'- 2 H 6-核呋喃糖苷6（ 82％的人提供了合成氘核糖核苷用于RNA或DNA合成的关键组成部分。然后将化合物6与甲硅烷基尿嘧啶，N
• Synthesis and hybridizing properties of P-stereodefined chimeric [PS]-{DNA:RNA} and [PS]-{DNA:(2′-OMe)-RNA} oligomers
  作者：Katarzyna Jastrzębska、Anna Maciaszek、Rafał Dolot、Agnieszka Tomaszewska-Antczak、Barbara Mikołajczyk、Piotr Guga

  DOI：10.1039/d2ra04855h

  日期：——

  the solid-phase synthesis of phosphorothioate dinucleotides (MNPST and NPST, respectively), which were subsequently hydrolyzed with RP-selective phosphodiesterase svPDE and SP-selective nuclease P1 to determine the absolute configuration of the phosphorus atoms. P-Stereodefined phosphorothioate ([PS]) 10-mer chimeric oligomers [PS]-DNA:(2′-OMe)-RNA} and isosequential [PS]-DNA:RNA} containing two MNPS

  合成了 2'-OMe-核糖核苷和 2'- O -TBDMS-核糖核苷（分别为M N-OTP 和T N-OTP；核碱基保护）的 Oxathiaspirlane 衍生物，并分离为纯 P-非对映体。 X射线分析显示TA -OTP的快速洗脱非对映异构体中磷原子的R P绝对构型。 M N-OTP 和T N-OTP 的快速和慢速洗脱 P-非对映体用于硫代磷酸二核苷酸（分别为M N PS T 和 N PS T）的固相合成，随后用R水解P-选择性磷酸二酯酶 svPDE 和S P-选择性核酸酶 P1 确定磷原子的绝对构型。 P-立体定义硫代磷酸酯 ([PS]) 10 聚体嵌合寡聚物 [PS]-DNA:(2'-OMe)-RNA} 和含有两个M N PS或 N PS单元的等序列 [PS]-DNA:RNA}被合成。 对它们与 Watson-Crick 配对 DNA 基质的复合物进行的熔化实验表明， M N PS或