3'-O-tert-butydiphenylsilyl-N⁴-benzoyl-2'-deoxycytidine | 166758-08-3

• 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: 3'-O-tert-butydiphenylsilyl-N⁴-benzoyl-2'-deoxycytidine
• 英文别名: 4-N-benzoyl-3'-O-tert-butyldiphenylsilyl-2'-deoxycytidine；N4-benzoyl-3'-O-tert-butyldiphenylsilyl-2'-deoxycytidine；N-[1-[(2R,4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 166758-08-3
• 化学式: C₃₂H₃₅N₃O₅Si
• 分子量: 569.732
• InChiKey: RECRILYRJFVHKF-YIKNKFAXSA-N

物化性质

• 熔点：
  96-100 °C
• 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：

  3'-O-tert-butydiphenylsilyl-N⁴-benzoyl-2'-deoxycytidine 在 吡啶 、 N-碘代丁二酰亚胺 、 水 、 potassium carbonate 、 二甲基亚砜 、 四乙基碳酸氢铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 N4-benzoyl-3-O'-tert-butyldiphenylsilyl-2'-deoxy-4'-methoxycytidine
  参考文献：
  名称：

  嘌呤4'-烷氧基-2'-脱氧核苷的直接合成：混合嘌呤-嘧啶4'-烷氧基寡聚脱氧核苷酸作为新的RNA模仿物的首次报道。

  摘要：

  通过N-碘代琥珀酰亚胺促进的烷氧基化，水解和还原反应，然后转化为亚磷酰胺单体进行固相分三步，由核苷4'-5'-烯醇乙酸酯高效地制备了嘌呤和嘧啶4'-烷氧基-2'-脱氧核苷寡核苷酸的合成。以普遍的N型（RNA样）构象为特征的经过完全修饰的4'-烷氧基寡聚脱氧核苷酸表现出优异的化学和核酸酶抗性以及出色的杂交特性，具有很强的RNA选择性杂交趋势，表明其潜在的应用前景。反义技术中的4'-烷氧基-寡脱氧核苷酸。

  DOI：

  10.1021/acs.orglett.5b01430
• 作为产物：
  描述：

  N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷 在 咪唑 、 三氯乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3'-O-tert-butydiphenylsilyl-N⁴-benzoyl-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides

  摘要：

  An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.

  DOI：

  10.1021/jo00121a037

文献信息

• Synthesis of Disaccharide Nucleosides by the<i>O</i>-Glycosylation of Natural Nucleosides with Thioglycoside Donors
  作者：Shin Aoki、Taketo Fukumoto、Taiki Itoh、Masayuki Kurihara、Shigeto Saito、Shin-ya Komabiki

  DOI：10.1002/asia.201403319

  日期：2015.3

  Disaccharide nucleosides constitute an important group of naturally‐occurring sugar derivatives. In this study, we report on the synthesis of disaccharide nucleosides by the direct O‐glycosylation of nucleoside acceptors, such as adenosine, guanosine, thymidine, and cytidine, with glycosyl donors. Among the glycosyl donors tested, thioglycosides were found to give the corresponding disaccharide nucleosides

  二糖核苷是天然存在的糖衍生物的重要组成部分。在这项研究中，我们报道了通过核苷受体（如腺苷，鸟苷，胸苷和胞苷）与糖基供体的直接O-糖基化来合成二糖核苷。在测试的糖基供体中，发现硫代糖苷可以使用对甲苯磺酰氯（TolSCl）和三氟甲磺酸银（AgOTf）作为促进剂，以上述核苷受体以中等至高化学产率提供相应的二糖核苷。通过1 H NMR光谱实验检查了这些启动子与核苷受体的相互作用。
• Geminal hydroxy phosphonate derivatives of nucleosides: A novel class of nucleoside 5′-monophosphate analogues
  作者：Šárka Králı́ková、Miloš Budĕšı́nský、Milena Masojı́dková、Ivan Rosenberg

  DOI：10.1016/s0040-4039(99)02107-3

  日期：2000.2

  A novel type of phosphonate-based, isopolar, nonisosteric 5′-nucleotide analogue, the nucleoside 5′-hydroxy phosphonates, was prepared by Abramov nucleophilic addition of various phosphorous acid esters to nucleoside 5′-aldehydes. The newly formed compounds are distinguished by chirality of the 5′-carbon atom. The configuration of the 5′-epimers was assigned from NMR spectra.

  通过将各种亚磷酸酯亲核加成到核苷5'-醛上，制备了一种新型的基于膦酸酯的，等极性，非等规的5'-核苷酸类似物，核苷5'-羟基膦酸酯。新形成的化合物的特征在于5'-碳原子的手性。5'-差向异构体的构型由NMR光谱确定。
• Nucleoside 5′-C-phosphonates: reactivity of the α-hydroxyphosphonate moiety
  作者：Šárka Králíková、Miloš Buděšínký、Milena Masojídková、Ivan Rosenberg

  DOI：10.1016/j.tet.2006.03.008

  日期：2006.5

  We found that various dialkyl phosphites, dialkyl trimethylsilyl phosphites, and tris-trimethylsilyl phosphite reacted smoothly with nucleoside 5'-aldehydes to afford epimeric nucleoside 5'-C-phosphonates in high yields. A number of these compounds in both the 2'-deoxyribo and ribo series were prepared. In the case of 2'-deoxythymidine-5'-aldehyde, a thorough study was made on the influence of the 5'-hydroxyl protecting group, type of phosphite, base, and solvent, on the yield and epimeric ratio of the resulting 5'-hydroxyphosphonates. Partial stereoselectivity in favour of either R or S epimers was observed. An attempt to transform the alpha-hydroxyl of the phosphonate moiety into a halo or azido moiety was not Successful. Only intramolecular substitution reaction of the mesyloxy group for an alkoxy residue of the 2-hydroxyethyl ester took place in a low yield. (c) 2006 Elsevier Ltd. All rights reserved.
• Rodionov; Efimtseva; Fomicheva, Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 3, p. 179 - 185
  作者：Rodionov、Efimtseva、Fomicheva、Padyukova、Mikhailov

  DOI：——

  日期：——
• Triarylmethyl Substituted 4,5-Dicyanoimidazoles as Activators for Rp-Diastereoselective Synthesis of TpN Dinucleoside Methylphosphonates
  作者：Peter Schell、Wolfgang H. G. Laux、Joachim W. Engels

  DOI：10.1080/07328319908044654

  日期：1999.6

  2-Triarylmethyl-4,5-dicyanoimidazoles 1-3 were synthesized and tested as activators in the methylphosphonamidite approach. TpN dinucleoside methylphosphonates generated showed diastereoselectivity of up to 8 / 1 (Rp / Sp). The influence of the different triarylmethyl substituents on diastereoselectivity is shown.