2,3,5-tri-O-benzoyl-1-bromo-D-ribofuranosyl cyanide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzoyl-1-bromo-D-ribofuranosyl cyanide
• 英文别名: [(2R,3R,4R)-3,4-dibenzoyloxy-5-bromo-5-cyanooxolan-2-yl]methyl benzoate
• 化学式: C₂₇H₂₀BrNO₇
• 分子量: 550.362
• InChiKey: XCVJLNUSYSJOGE-IANNTBFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-1-bromo-D-ribofuranosyl cyanide 在 咪唑 、 ammonium hydroxide 、 氰化汞 作用下， 以 甲醇 、 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 1(5-O-tert-butyldimethylsilyl-1-cyano-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and structure determination of the first 1′-C-cyano-β-D-nucleosides

  摘要：

  The 1'-cyano -2',3'-D-unsaturated nucleoside 8 was synthesised according to the following steps. Photobromination of the ribofuranosyl cyanide 1 using N-bromosuccinimide (NBS) as a radical source gave the two isomers of the new C-1 gem disubstituted sugar 2. Its condensation with silylated thymine afforded the blocked nucleoside 3, the stereochemistry and molecular shape of which were deduced from NMR studies and molecular simulation. After deprotection of 3 into 4, thiocarbonylation of the silylated derivative 5, followed by olefination of 6, led to 7 which was deblocked to the 1'-cyano substituted d4T 8.

  DOI：

  10.1016/s0040-4020(01)96264-7
• 作为产物：
  描述：

  (2R,3R,4S)-2-((benzoyloxy)methyl)-5-cyanotetrahydrofuran-3,4-diyl dibenzoate 在 溴 作用下， 以 四氯化碳 为溶剂， 以70%的产率得到2,3,5-tri-O-benzoyl-1-bromo-D-ribofuranosyl cyanide
  参考文献：
  名称：

  [EN] NUCLEOSIDES AND NUCLEOTIDES ANALOGS AS ANTIVIRAL AGENTS
  [FR] ANALOGUES DE NUCLÉOSIDES ET DE NUCLÉOTIDES UTILISÉS EN TANT QU'AGENTS ANTIVIRAUX

  摘要：

  公开号：

  WO2022217153A3

文献信息

• Synthesis of 1′-<i>C</i>-Cyano Pyrimidine Nucleosides and Characterization as HCV Polymerase Inhibitors
  作者：Thorsten A. Kirschberg、Michael Mish、Neil H. Squires、Sebastian Zonte、Evangelos Aktoudianakis、Sammy Metobo、Thomas Butler、Xie Ju、Aesop Cho、Adrian S. Ray、Choung U. Kim

  DOI：10.1080/15257770.2015.1075550

  日期：2015.11.2

  Ribose modified 1′-C-cyano pyrimidine nucleosides were synthesized. A silver triflate mediated Vorbrüggen reaction was used to generate the nucleoside scaffold and follow-up chemistry provided specific ribose modified analogs. Nucleosides and phosphoramidate prodrugs were tested for their anti-HCV activity.

  合成了核糖修饰的1'- C-氰基嘧啶核苷。使用三氟甲磺酸银介导的Vorbrüggen反应生成核苷支架，后续化学反应提供了特定的核糖修饰类似物。测试了核苷和氨基磷酸酯前药的抗HCV活性。
• 1'-SUBSTITUTED PYRIMIDINE N-NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT
  申请人：Cho Aesop

  公开号：US20120263678A1

  公开（公告）日：2012-10-18

  Provided are compounds of Formula I: nucleosides, nucleoside phosphates and prodrugs thereof, wherein R 6 is CN, ethenyl, 2-haloethen-1-yl, or (C 2 -C 8 )-alkyn-1-yl. The compounds, compositions, and methods provided are useful for the treatment of Flaviviridae virus infections.

  提供的是Formula I的化合物：核苷、核苷酸磷酸酯和它们的前药，其中R6是CN、乙烯基、2-卤乙烯基或(C2-C8)-烷炔基。提供的化合物、组合物和方法对于治疗黄病毒科病毒感染是有用的。
• Stereoselective bromination of β-ribofuranosyl amide. Enantioselective synthesis of (+)-hydantocidin
  作者：Philip M. Harrington、Michael E. Jung

  DOI：10.1016/s0040-4039(00)77049-3

  日期：1994.7

  The synthesis of hydantocidin, a potent herbicidal natural product, is highlighted by a stereoselective bromination of β-D-ribofuranosyl amide to give only the α-bromo β-amide and subsequent spirocyclization about the anomeric position with silver cyanate to form the hydantoin moiety.

  Hydantocidin是一种有效的除草天然产物，其合成通过β-D-呋喃呋喃糖基酰胺的立体选择性溴化作用而得到，仅得到α-溴β-酰胺，随后在异氰酸酯位置与氰化银进行螺环化反应，形成了乙内酰脲部分。
• [EN] 4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES À BASE DE NUCLÉOSIDES ET DE NUCLÉOTIDES CONTENANT DU 4'-HALOGÈNE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2022174194A1

  公开（公告）日：2022-08-18

  Disclosed are halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of viral infections. Such viral infections can include tongaviridae, bunyaviridae, arenaviridae, coronaviridae, flaviviridae, picornaviridae, Eastern, Western, and Venezuelan Equine Encephalitis (EEE, WEE and VEE, respectively), Chikungunya fever (CHIK), Ebola, Influenza, RSV, and Zika virus infections.

  本文披露了含卤素的核苷酸和核苷治疗组合物及其相关用途。在某些实施例中，本文涉及治疗或预防病毒感染。这种病毒感染可以包括东部、西部和委内瑞拉马脑炎病毒（EEE、WEE和VEE），Chikungunya热（CHIK），埃博拉，流感，RSV和寨卡病毒感染，以及tongaviridae，bunyaviridae，arenaviridae，coronaviridae，flaviviridae和picornaviridae等。
• Synthesis and structure determination of the first 1′-C-cyano-β-D-nucleosides
  作者：Valérie Uteza、Guo-Rong Chen、Jérémie Le Quan Tuoi、Gérard Descotes、Bernard Fenet、Annie Grouiller

  DOI：10.1016/s0040-4020(01)96264-7

  日期：1993.9

  The 1'-cyano -2',3'-D-unsaturated nucleoside 8 was synthesised according to the following steps. Photobromination of the ribofuranosyl cyanide 1 using N-bromosuccinimide (NBS) as a radical source gave the two isomers of the new C-1 gem disubstituted sugar 2. Its condensation with silylated thymine afforded the blocked nucleoside 3, the stereochemistry and molecular shape of which were deduced from NMR studies and molecular simulation. After deprotection of 3 into 4, thiocarbonylation of the silylated derivative 5, followed by olefination of 6, led to 7 which was deblocked to the 1'-cyano substituted d4T 8.