2(S)-(O-benzoylmethyl)tetrahydrofuran-4(R)-ol | 143191-75-7

• 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(S)-(O-benzoylmethyl)tetrahydrofuran-4(R)-ol
• 英文别名: [(2S,4R)-4-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 143191-75-7
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: CAPOIHIIOBAKOL-MNOVXSKESA-N

物化性质

• 沸点：
  376.2±17.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2(S)-(O-benzoylmethyl)tetrahydrofuran-4(R)-ol 在 吡啶 、 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 4(S)-(6-amino-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran
  参考文献：
  名称：

  Zintek, Lawrence B.; Jeon, Geun Sook; Nair, Vasu, Heterocycles, 1994, vol. 37, # 3, p. 1853 - 1864

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 盐酸 、 三乙基硅烷 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 三正丁基氢锡 、 N,N'-硫羰基二咪唑 、 六甲基二硅氮烷 作用下， 以 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 生成 2(S)-(O-benzoylmethyl)tetrahydrofuran-4(R)-ol
  参考文献：
  名称：

  Zintek, Lawrence B.; Jeon, Geun Sook; Nair, Vasu, Heterocycles, 1994, vol. 37, # 3, p. 1853 - 1864

  摘要：

  DOI：

文献信息

• An improved method for the synthesis of anhydroalditols
  作者：Arlen Jeffery、Vasu Nair

  DOI：10.1016/0040-4039(95)00618-m

  日期：1995.5

  An improved synthesis of anhydroalditols through reductive cleavage of acetylated carbohydrates is reported. The procedure appears to have generality. Ring rearrangements, which complicate some other reported procedures for the preparation of anhydroalditols, were not observed. The acetate protecting groups used were stable under the reaction conditions employed.

  据报道，通过乙酰化碳水化合物的还原裂解，脱水醛糖醇的合成得到改善。该过程似乎具有普遍性。没有观察到环重排，这使制备脱水醛糖醇的其他一些报道的过程复杂化。所用的乙酸酯保护基在所用的反应条件下是稳定的。
• A Thymidine Phosphorylase-Stable Analogue of BVDU with Significant Antiviral Activity
  作者：Sven Guenther、Jan Balzarini、Erik De Clercq、Vasu Nair

  DOI：10.1021/jm025569k

  日期：2002.12.1

  (E)-5-(2-Bromovinyl)isodideoxyuridine (BVisoDDU), synthesized on the basis of molecular modeling, is selectively active against HSV-1 (three different strains) but inactive against HSV-2. Unlike BVDU, BVisoDDU is completely resistant to cleavage by thymidine phosphorylase. BVisoDDU is also the first nucleoside analogue lacking OH groups at both the 2'- and 3'-position that shows pronounced activity against HSV-1 replication.

  （E）-5-（2-溴乙烯基）等离子体脱氧尿苷二磷酸酯（BVissoDDU），基于分子建模合成了这种新合成的核苷酸类药物，它对HSV-1（三株不同的变种）具有高度选择性抑制作用，而对HSV-2无效。与BVDU不同，BVissoDDU完全耐受胸腺苷二磷酸水解酶的分解。此外，BVissoDDU是第一个在Structure上缺乏2'-和3'-羟基的核苷酸类药物，并且显示出显著的抗HSV-1复制活性。
• 3′-substituted methyl or alkynyl nucleosides nucleotides for the treatment of HCV
  申请人：IDENIX PHARMACEUTICALS LLC

  公开号：US10202411B2

  公开（公告）日：2019-02-12

  Provided herein are compounds, compositions and methods for the treatment of Flaviviridae infections, including HCV infections. In certain embodiments, compounds and compositions of nucleoside derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents. In certain embodiments, the compounds are 3′-substituted methyl or alkynyl nucleosides of Formula I: (I); or a pharmaceutically acceptable salt, solvate, stereoisomeric form, tautomeric form or polymorphic form thereof, wherein Base, PD, RA, RB1, RB2, RC and Z are as defined herein.

  本文提供了用于治疗黄病毒科感染（包括 HCV 感染）的化合物、组合物和方法。在某些实施方案中，公开了核苷衍生物的化合物和组合物，可单独使用或与其他抗病毒药物联合使用。在某些实施方案中，所述化合物为式I的3′-取代甲基或炔基核苷：(I)；或其药学上可接受的盐、溶液剂、立体异构体形式、同分异构体形式或多晶型形式，其中Base、PD、RA、RB1、RB2、RC和Z如本文所定义。
• Compositions and methods for modulating RNA
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US20020160972A1

  公开（公告）日：2002-10-31

  Compositions and methods for modulating the activity of RNA are disclosed. In accordance with preferred embodiments, antisense compositions are prepared comprising targeting and reactive portions. The reactive portions preferably comprise one or two imidazole functionalities conjugated to the targeting oligonucleotide via linkers with or without intervening intercalating moieties. Therapeutics, diagnostics and research methods also are disclosed, as are synthetic nucleosides and nucleoside fragments that can be elaborated into oligonucleotides.

  本文公开了调节 RNA 活性的组合物和方法。根据优选的实施方案，反义组合物由靶向部分和反应部分组成。反应部分优选由一个或两个咪唑官能团组成，通过连接体与靶向寡核苷酸连接，中间有或没有插层分子。此外，还公开了治疗、诊断和研究方法，以及可制成寡核苷酸的合成核苷和核苷片段。
• Novel isomeric dideoxynucleosides as potential antiviral agents
  作者：Pascal J. Bolon、Todd B. Sells、Zoraida M. Nuesca、David F. Purdy、Vasu Nair

  DOI：10.1016/s0040-4020(01)85259-5

  日期：1994.1

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.