2,3,5-Tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-arabinofuranose | 31598-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-Tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-arabinofuranose
• 英文别名: 2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-beta-D-arabinofuranose；[(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl] 4-nitrobenzoate
• CAS: 31598-80-8
• 化学式: C₃₃H₃₁NO₈
• 分子量: 569.611
• InChiKey: VBDBDZHLJKDSSB-QFBUMDDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  109
• 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-benzyl-1-O-(p-nitrobenzoyl)-β-D-arabinofuranose 在 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 以98%的产率得到2,3,5-Tri-O-benzyl-1-brom-D-arabinofuranose
  参考文献：
  名称：

  Sugar derivatives of macrolides

  摘要：

  本发明涉及用于治疗移植抗拒、自身免疫疾病和真菌病的大环化合物的糖衍生物。

  公开号：

  US05747465A1

文献信息

• ara-7-Desazaxanthosin — ein Xanthin-Nucleosid mit stabiler N-glycosylischer Bindung
  作者：Frank Seela、Ulrich Liman

  DOI：10.1002/jlac.198419840210

  日期：1984.2.13

  ara-7-Desazaxanthosin (2) wurde durch Phasentransferglycosylierung von 2,4-Dimethoxy-7H-pyrrolo[2,3-d]pyrimidin (5b) mit der Halogenose 6 dargestellt. Von dem bei der Glycosylierung bevorzugt gebildeten β-Anomer 8 wurden die Benzylschutzgruppen mit Bortrichlorid entfernt und die 2,4-Dimethoxyreste mit Säure abgespalten. Das 7-Desazapurin-Nucleosid 2 besitzt im Gegensatz zu Xanthosin (1a) eine bei saurer

  ARA -7- deazaxanthosine（2）的制备是通过相转移糖基化的2,4-二甲氧基- 7 ħ吡咯并[2,3- d ]嘧啶（图5b与halogenose）6。用三氯化硼除去优选在糖基化反应中形成的β-端基异构体8的苄基保护基，并用酸分离出2，4-二甲氧基。与黄嘌呤（1a）相反，7-脱氮嘌呤核苷2具有在酸水解时稳定的N-糖基键。通过比较嘌呤核苷与2的动力学参数描述了质子催化水解的反应机理，也解释了吡咯并[2,3- d ]嘧啶核苷2的稳定性。
• Anticancer and antiviral activity of
  申请人：The United States of America as represented by the Department of Health,

  公开号：US04188378A1

  公开（公告）日：1980-02-12

  A method of utilizing 9-.beta.-D-arabinofuranosyl-2-fluoroadenine, known as 2-F-AraA (NSC 118218), in the treatment of murine leukemia and as an antiviral agent for DNA viruses, such as DNA viruses Herpes Simplex Virus Type I and Vaccinia virus grown in H.Ep-2 cells in culture. An operable dosage for utilization of 2-F-AraA is a treatment span of 1-10 days with the dosage 2-8 times per day at 8-400 mg/kg/dose. It has been further found that a single dosage on days 1, 5, and 9 based on a 10-day treatment schedule gave satisfactory results.

  利用9-β-D-阿拉伯呋喃糖基-2-氟腺嘌呤，即2-F-AraA（NSC 118218），用于治疗小鼠白血病，并作为DNA病毒的抗病毒剂，如DNA病毒单纯疱疹病毒I型和培养在H.Ep-2细胞中的天花病毒。2-F-AraA的可操作用量为1-10天的治疗时间，每天2-8次，每次8-400毫克/千克。进一步发现，在一个为期10天的治疗计划中，第1、5和第9天的单剂量给出了令人满意的结果。
• [EN] METHOD FOR THE MANUFACTURE OF 2-FLUORO-ARA-ADENINE<br/>[FR] PROCÉDÉ DE FABRICATION DE 2-FLUORO-ARA-ADÉNINE
  申请人：ALCAFLEU MAN GMBH & CO KG

  公开号：WO2010130778A1

  公开（公告）日：2010-11-18

  A method is described for the manufacture of pure 2-fluoro-ara-adenine of Formula (I) from 2-fluoro-ara-adenine triacetate using potassium carbonate (K2CO3), wherein the 2-fluoro-ara-adenine has a reduced dimer contents, as well as the compound 2-fluoro-ara-adenine having a dimer contents of ≤ 0,3 %.

  本文描述了一种制备纯2-氟-阿拉-腺嘌呤（化学式（I））的方法，该方法使用碳酸钾（K2CO3）从2-氟-阿拉-腺嘌呤三乙酸酯制备，其中2-氟-阿拉-腺嘌呤的二聚体含量降低，同时2-氟-阿拉-腺嘌呤化合物的二聚体含量≤0.3％。
• SYNTHESIS OF HALOGEN-SUBSTITUTED 3-DEAZAADENOSINE AND 3-DEAZAGUANOSINE ANALOGUES AS POTENTIAL ANTITUMOR/ANTIVIRAL AGENTS
  作者：Mao-Chin Liu、Mei-Zhen Luo、Diane Mozdziesz、Tai-Shun Lin?1、Ginger Dutschman、Elizabeth Gullen、Yung-Chi Cheng、Alan Sartorelli

  DOI：10.1081/ncn-100108327

  日期：——

  Various 2-halogen-substituted analogues (38, 39, 43 and 44), 3-halogen-substituted analogues (51 and 52), and 2',3'-dihalogen-substituted analogues (57-60) of 3-deazaadenosine and 3-halogen-substituted analogues (61 and 62) of 3-deazaguanosine have been synthesized as potential anticancer and/or antiviral agents. Among these compounds, 3-deaza-3-bromoguanosine (62) showed significant cytotoxicity against L1210, P388, CCRF-CEM and B16F10 cell lines in vitro, producing IC50 values of 3, 7, 9 and 7 muM, respectively. Several 3-deazaadenosine analogues (38, 51, 57 and 59) showed moderate to weak activity against hepatitis B virus.
• Synthesis of 3-hydroxy-2- and -4-pyridone nucleosides as potential antitumor agents
  作者：David T. Mao、John S. Driscoll、Victor E. Marquez

  DOI：10.1021/jm00368a010

  日期：1984.2

  The ribo- and arabinofuranosyl nucleosides of antitumor active 2- and 4-pyridones 1a and 2a were prepared by direct condensation of the silylated bases with either 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (4a) or 2,3,5-tri-O-benzyl-1-p-nitrobenzoyl-D-arabinofuranose (7) in the presence of trimethylsilyl triflate (Me3SiOTf). In the case of the arabinofuranosyl nucleosides, separation of the alpha and beta anomers was accomplished at the stage of O-benzyl-protected compounds (8b + 9b, and 10b + 11b) after chemical functionalization of the 3-hydroxy group of the pyridone aglycons with acetyl and benzyl groups, respectively. Deblocking of the protected ribo- and arabinofuranosyl nucleosides was performed by the standard methods. In vitro activity against P-388 cells in culture indicated that the 4-pyridone riboside 6d was the most active member of the series with a twofold lower ID50 than the parent pyridone 2a. However, this and all the other compounds tested in this series showed no activity against the in vivo model system of murine P-388 leukemia at doses ranging from 25 to 400 mg/kg qd 1-5.