N⁴-benzoyl-5’-O-levulinyl-β-D-cytidine | 1245770-94-8

• 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: N⁴-benzoyl-5’-O-levulinyl-β-D-cytidine
• 英文别名: N⁴-benzoyl-5'-O-levulinoyl-β-D-cytidine；[(2R,3S,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl 4-oxopentanoate
• CAS: 1245770-94-8
• 化学式: C₂₁H₂₃N₃O₈
• 分子量: 445.429
• InChiKey: JSRDWSSIZHOEKW-VXXKDZQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  155
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯甲酰胞苷 、 acetonoxime levulinate 在 Candida antarctica lipase B 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以93%的产率得到N⁴-benzoyl-5’-O-levulinyl-β-D-cytidine
  参考文献：
  名称：

  合成 2',3'-双脱氧核苷和 2',3'-Didehydro-2',3'-双脱氧核苷衍生物的可持续方案

  摘要：

  将核糖核苷转化为 2',3'-二脱氧核苷和 2',3'-二脱氢-2',3'-二脱氧核苷衍生物的改进方案，包括抗 HIV 药物司他夫定 (d4T)、扎西他滨 (ddC) 和去羟肌苷 (ddI) 成立。该过程涉及使用环保和低成本的试剂对黄原酸盐进行自由基脱氧。溴乙烷或 3-溴丙腈是制备核糖核苷 2',3'-双黄原酸酯的首选烷化剂。在随后的自由基脱氧反应中，三（三甲基甲硅烷基）硅烷和 1,1'-偶氮二（环己烷甲腈）分别被用来代替有害的 Bu 3 SnH 和 AIBN。此外，在 5'- O的脱保护步骤中，TBAF 取代了樟脑磺酸。-甲硅烷基醚基团和一种酶（腺苷脱氨酶）用于将 2',3'-二脱氧腺苷转化为 2',3'-二脱氧肌苷 (ddI)，产率很高。

  DOI：

  10.3390/molecules27133993

文献信息

• Enzymatic Parallel Kinetic Resolution of Mixtures of <scp>d</scp>/<scp>l</scp> 2′-Deoxy and Ribonucleosides: An Approach for the Isolation of β-<scp>l</scp>-Nucleosides
  作者：Saúl Martínez-Montero、Susana Fernández、Yogesh S. Sanghvi、Vicente Gotor、Miguel Ferrero

  DOI：10.1021/jo101368z

  日期：2010.10.1

  We have developed a lipase-catalyzed parallel kinetic resolution of mixtures of beta-D/L-nucleosides. The opposite selectivity during acylation exhibited by Pseudomonas cepacia lipase (PSL-C) with beta-D- and beta-L-nucleosides furnished acylated compounds that have different R-f values. As a consequence, isolation of both products was achieved by simple column chromatography. Computer modeling of the transition-state analogues during acylation of beta-D- and beta-L-2'-deoxycytidine with PSL-C was carried out to explain the high selectivity. PSL-C favored the 3'-O-levulination of the beta-D enantiomer, whereas the 5'-OH group was acylated in 2'-deoxy-beta-L-cytidine. In both cases, the cytosine base was placed in the alternate hydrophobic pocket of PSL's substrate-binding site, where it can form extra hydrogen bonds (in addition to the five essential catalytically relevant hydrogen bonds) that stabilize these intermediates catalyzing the selective acylation of beta-D/L-nucleosides.
• Sustainable Protocol for the Synthesis of 2′,3′-Dideoxynucleoside and 2′,3′-Didehydro-2′,3′-dideoxynucleoside Derivatives
  作者：Virginia Martín-Nieves、Yogesh S. Sanghvi、Susana Fernández、Miguel Ferrero

  DOI：10.3390/molecules27133993

  日期：——

  ribonucleosides into 2’,3’-dideoxynucleoside and 2’,3’-didehydro-2’,3’-dideoxynucleoside derivatives, including the anti-HIV drugs stavudine (d4T), zalcitabine (ddC) and didanosine (ddI), was established. The process involves radical deoxygenation of xanthate using environmentally friendly and low-cost reagents. Bromoethane or 3-bromopropanenitrile was the alkylating agent of choice to prepare the

  将核糖核苷转化为 2',3'-二脱氧核苷和 2',3'-二脱氢-2',3'-二脱氧核苷衍生物的改进方案，包括抗 HIV 药物司他夫定 (d4T)、扎西他滨 (ddC) 和去羟肌苷 (ddI) 成立。该过程涉及使用环保和低成本的试剂对黄原酸盐进行自由基脱氧。溴乙烷或 3-溴丙腈是制备核糖核苷 2',3'-双黄原酸酯的首选烷化剂。在随后的自由基脱氧反应中，三（三甲基甲硅烷基）硅烷和 1,1'-偶氮二（环己烷甲腈）分别被用来代替有害的 Bu 3 SnH 和 AIBN。此外，在 5'- O的脱保护步骤中，TBAF 取代了樟脑磺酸。-甲硅烷基醚基团和一种酶（腺苷脱氨酶）用于将 2',3'-二脱氧腺苷转化为 2',3'-二脱氧肌苷 (ddI)，产率很高。