L-呋喃核糖 | 41546-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: L-呋喃核糖
• 英文名称: L-ribose
• 英文别名: L-ribofuranose；(3S,4R,5S)-5-(hydroxymethyl)oxolane-2,3,4-triol
• CAS: 41546-21-8
• 化学式: C₅H₁₀O₅
• 分子量: 150.131
• InChiKey: HMFHBZSHGGEWLO-OWMBCFKOSA-N

物化性质

• 沸点：
  375.4±42.0 °C(Predicted)
• 密度：
  1.681±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  L-呋喃核糖 在 三氟甲磺酸 、 硫酸 、 lithium carbonate 作用下， 以 乙酸甲酯 为溶剂， 20.0~115.0 ℃ 、3.0 kPa 条件下， 反应 16.5h， 生成 methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of Methyl 1-(2,3,5-Tri-O-acetyl-β-l-ribofuranosyl)-1,2,4- triazole-3-carboxylate from l-Ribose:  From a Laboratory Procedure to a Manufacturing Process

  摘要：

  A two-step manufacturing process for methyl 1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (1) was developed. In step 1, L-ribose was converted to a beta/alpha mixture of 1,2,3,5-tetra-O-acetyl-L-ribofuranoses (2 and 4). The step contained four chemical transformations and was completed in "one-pot" in approximately 95% yield. The crude step 1 product was reacted with methyl 1,2,4-triazole-3-carboxylate (3) in step 2 to produce 1. The successful utilization of both isomers (2 and 4) in step 2 offered advantages of higher overall yield and a much simplified process by eliminating the isolation of pure 2. The process was successfully scaled up to the pilot plant and subsequently in a manufacturing campaign using commercial production facilities.

  DOI：

  10.1021/op050051m
• 作为产物：
  描述：

  L-uridine 在 水 作用下， 生成 L-呋喃核糖
  参考文献：
  名称：

  异恶唑啉-5-酮苷的合成和光敏性†

  摘要：

  描述了一种从未保护的碳水化合物开始合成异恶唑啉-5-酮糖苷的新方法。使用D-构型的葡萄糖，木糖，麦芽糖，果糖，核糖和2-脱氧核糖探索一锅合成方案的底物范围。合成了天然存在的2-（β- D-吡喃葡萄糖基）-3-异恶唑啉-5-酮和四种衍生自木糖，麦芽糖和果糖的新型异恶唑啉-5-酮糖苷，并通过快速色谱法纯化。根据化学结构，光物理性质以及pH稳定性对化合物进行了表征。将合成的糖苷的光水解速率与尿苷作为标准进行比较，以确定水中光反应的量子产率。

  DOI：

  10.1039/c5ob00244c

文献信息

• Total Chemical Synthesis and Folding of All-<scp>l</scp> and All-<scp>d</scp> Variants of Oncogenic KRas(G12V)
  作者：Adam M. Levinson、John H. McGee、Andrew G. Roberts、Gardner S. Creech、Ting Wang、Michael T. Peterson、Ronald C. Hendrickson、Gregory L. Verdine、Samuel J. Danishefsky

  DOI：10.1021/jacs.7b02988

  日期：2017.6.7

  of hydrophobic binding pockets. Herein, we report a total chemical synthesis of all-l- and all-d-amino acid biotinylated variants of oncogenic mutant KRas(G12V). The protein is synthesized using Fmoc-based solid-phase peptide synthesis and assembled using combined native chemical ligation and isonitrile-mediated activation strategies. We demonstrate that both KRas(G12V) enantiomers can successfully

  Ras 蛋白是参与细胞增殖和存活调节的重要 GTP 酶。Ras 的突变致癌形式会改变效应子结合和先天 GTP 酶活性，导致下游信号转导失调。Ras 的突变形式与大约 30% 的人类癌症有关。尽管数十年来一直致力于开发直接 Ras 抑制剂，但 Ras 长期以来一直被认为是“不可成药的”，因为它对 GTP 具有高亲和力并且缺乏疏水性结合袋。在此，我们报告了致癌突变体 KRas(G12V) 的全 L-和全 D-氨基酸生物素化变体的全化学合成。该蛋白质使用基于 Fmoc 的固相肽合成法合成，并使用组合的天然化学连接和异腈介导的激活策略进行组装。我们证明两种 KRas(G12V) 对映体都可以成功折叠并结合核苷酸底物和结合配偶体，并具有可观察到的对映体歧视。通过证明镜像形式的 KRas 与其相应的对映体三磷酸核苷酸结合的功能能力，本研究为利用该材料进行进一步的生化研究奠定了基础。特别是，这种蛋白质将使镜像酵母表面展示实验能够识别致癌
• Synthesis of beta-L-2'-deoxy nucleosides
  申请人：Storer Richard

  公开号：US20050059632A1

  公开（公告）日：2005-03-17

  An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro- 1 -furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

  提供了一种改进的2'-改性核苷和2'-脱氧核苷的制备工艺，例如，β-L-2'-脱氧胸苷（LdT）。特别是，改进的工艺针对的是2'-脱氧核苷的合成，该合成可能使用不同的起始材料，但都通过氯糖中间体或通过2,2'-脱水-1-呋喃糖核苷中间体进行。当使用2,2'-脱水-1-呋喃糖碱基中间体时，会采用还原剂（如Red-Al）和隔离剂（如15-冠-5醚），它们能引起分子内位移反应，并形成所需核苷产品的高收率。本发明的一种替代工艺使用2,2'-脱水-1-呋喃糖碱基中间体而不使用隔离剂，也能以高收率获得2'-脱氧核苷。根据本发明制成的化合物可以作为制备其他核苷类似物的中间体，或者可以直接用作抗病毒和/或抗肿瘤剂。
• Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development
  作者：Scott A. Shaw、Balu Balasubramanian、Samuel Bonacorsi、Janet Caceres Cortes、Kevin Cao、Bang-Chi Chen、Jun Dai、Carl Decicco、Animesh Goswami、Zhiwei Guo、Ronald Hanson、W. Griffith Humphreys、Patrick Y. S. Lam、Wenying Li、Arvind Mathur、Brad D. Maxwell、Quentin Michaudel、Li Peng、Andrew Pudzianowski、Feng Qiu、Shun Su、Dawn Sun、Adrienne A. Tymiak、Benjamin P. Vokits、Bei Wang、Ruth Wexler、Dauh-Rurng Wu、Yingru Zhang、Rulin Zhao、Phil S. Baran

  DOI：10.1021/acs.joc.5b00632

  日期：2015.7.17

  Clopidogrel is a prodrug anticoagulant with active metabolites that irreversibly inhibit the platelet surface GPCR P2Y12 and thus inhibit platelet activation. However, gaining an understanding of patient response has been limited due to imprecise understanding of metabolite activity and stereochemistry, and a lack of acceptable analytes for quantifying in vivo metabolite formation. Methods for the

  氯吡格雷是具有活性代谢产物的前药抗凝剂，其不可逆地抑制血小板表面GPCR P2Y 12并因此抑制血小板活化。然而，由于对代谢物活性和立体化学的不精确了解，以及缺乏用于量化体内代谢物形成的可接受分析物，对患者反应的了解受到了限制。公开了用于产生氯吡格雷的所有生物活性代谢物，其立体化学分配以及通过三种概念上正交的途径开发稳定的分析物的方法。
• METHOD FOR PRODUCING THIOLANE SKELETON-TYPE GLYCOCONJUGATE, AND THIOLANE SKELETON-TYPE GLYCOCONJUGATE
  申请人：FUJIFILM Corporation

  公开号：US20160355536A1

  公开（公告）日：2016-12-08

  There is provided a production method of a compound represented by the following formula (II) through a step of reacting a compound represented by the following General Formula (I) with a sulfur compound. In General Formulas (I) and (II), R 1 represents a hydrogen atom or an acyl group, R 2 represents a hydrogen atom, a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R 3 represents a hydrogen atom or an acyloxy group, R 5 represents an alkyl group or an aryl group, and X represents a leaving group. Here, in a case where R 2 is a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R 3 is an acyloxy group.

  提供了一种通过将通用式（I）表示的化合物与硫化合物反应的步骤来制备通式（II）表示的化合物的生产方法。在通式（I）和（II）中，R1代表氢原子或酰基，R2代表氢原子、氟原子、酰氧基、芳基甲氧基、烯丙氧基、芳基甲氧羰氧基或烯丙氧羰氧基，R3代表氢原子或酰氧基，R5代表烷基或芳基，X代表离去基团。在R2为氟原子、酰氧基、芳基甲氧基、烯丙氧基、芳基甲氧羰氧基或烯丙氧羰氧基的情况下，R3为酰氧基。
• 2'3' CYCLIC DINUCLEOTIDES WITH PHOSPHONATE BOND ACTIVATING THE STING ADAPTOR PROTEIN
  申请人：INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ASCR,V.V.I.

  公开号：US20190185510A1

  公开（公告）日：2019-06-20

  The present disclosure relates to 2′3′ cyclic phosphonate dinucleotides of general formula (J), their pharmaceutically acceptable salts, their pharmaceutical composition and combinations of said substances and other medicaments or pharmaceuticals. The disclosure also relates to the use of said compounds for the treatment or prevention of diseases or conditions modifiable by STING protein modulation, such as cancer or viral, allergic and inflammatory diseases. In addition, these substances can be used as adjuvants in vaccines.

  本公开涉及一般式（J）的2′3′环磷酸二核苷酸，其药用可接受盐，其药物组合物以及所述物质与其他药物或药品的组合物。该公开还涉及使用所述化合物治疗或预防可通过STING蛋白调节改变的疾病或状况，如癌症或病毒性、过敏性和炎症性疾病。此外，这些物质可用作疫苗的辅助剂。