1-O-benzyl-α-D-ribofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-benzyl-α-D-ribofuranose
• 英文别名: (2R,3S,4R,5S)-2-(hydroxymethyl)-5-phenylmethoxyoxolane-3,4-diol
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: MBBBSHXQRFAIPA-KKOKHZNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  卡培他滨杂质25 、 苯甲醇 在 四溴化碳 、 三苯基膦 作用下， 反应 16.0h， 以24%的产率得到
  参考文献：
  名称：

  Organocatalyzed Direct Glycosylation of Unprotected and Unactivated Carbohydrates

  摘要：

  Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates is reported. This process is catalyzed by triphenylphosphine and tetrabromomethane at room temperature under neutral conditions. With this operationally simple protocol thermodynamically favored, glycosides were obtained in a very straightforward reaction.

  DOI：

  10.1021/ol402914v

文献信息

• Readily available carbohydrate-derived imines and amides as chiral ligands for asymmetric catalysis
  作者：Maria Cristina Pigro、Gabriella Angiuoni、Giovanni Piancatelli

  DOI：10.1016/s0040-4020(02)00510-0

  日期：2002.7

  easy and diastereoseletive strategy for the synthesis of a new tetrahydrofuranic chiral aldehyde and a new tetrahydrofuranic acid derived from d-ribose is reported. These compounds have been shown to be useful starting materials for obtaining a never described before class of iminic- and amidic-carbohydrate-based chiral ligands, endowed with stability to purification on silica flash column and to storage

  报道了一种容易且非对映异构的策略，用于合成新的四氢呋喃手性醛和衍生自d-核糖的新的四氢呋喃酸。这些化合物已显示是有用的起始原料，可用于获得从未描述过的亚胺基和亚胺基的基于碳水化合物的手性配体，具有在硅胶快速柱上纯化和储存的稳定性，并以存在立体异构体为特征中心α到亚胺键或亚胺键。讨论了从这些手性配体在模型反应中的应用获得的第一个结果，即将Et 2 Zn共轭添加到环己烯酮中。
• Method for producing a beta-D-ribofuranose derivative or an optical isomer thereof
  申请人：Ajinomoto Co., Inc.

  公开号：EP1260516A1

  公开（公告）日：2002-11-27

  The invention provides a method for efficiently producing β-D-ribofuranose derivatives or optical isomers thereof, useful as synthetic intermediates of pharmaceutical nucleic acid-series products. The method comprises a step of producing 1-O-benzyl-β-D-ribofuranose-2,3,5-triacetate or an optical isomer thereof by allowing β-D-ribofuranose-1,2,3,5-tetraacetate or an optical isomer thereof to react with benzyl alcohols in the presence of acid catalysts and a step of hydrolyzing the resulting 1-O-benzyl-β-D-ribofuranose-2,3,5-triacetate in the presence of a base to produce 1-O-benzyl-β-D-ribofuranose or an optical isomer thereof.

  本发明提供了一种高效生产β-D-核糖呋喃衍生物或其光学异构体的方法，该方法可用作制备药物核酸系列产品的合成中间体。该方法包括以下步骤：在酸催化剂的存在下，使β-D-核糖呋喃-1,2,3,5-四乙酸酯或其光学异构体与苄醇反应，以生产1-O-苄基-β-D-核糖呋喃-2,3,5-三乙酸酯或其光学异构体；在碱的存在下水解所得的1-O-苄基-β-D-核糖呋喃-2,3,5-三乙酸酯，以生产1-O-苄基-β-D-核糖呋喃或其光学异构体。
• Method for producing beta-D-ribofuranose derivatives or optical isomers thereof
  申请人：AJINOMOTO CO., INC.

  公开号：US20020187942A1

  公开（公告）日：2002-12-12

  The present invention provides a method for efficiently producing &bgr;-D-ribofuranose derivatives or optical isomers thereof, useful as synthetic intermediates of pharmaceutical nucleic acid-series products. The method comprises a step of producing 1-O-benzyl-&bgr;-D-ribofuranose-2,3,5-triacetate or an optical isomer thereof by allowing &bgr;-D-ribofuranose-1,2,3,5-tetraacetate or an optical isomer thereof to react with a benzyl alcohol in the presence of acid catalysts and a step of hydrolyzing the resulting 1-O-benzyl-&bgr;-D-ribofuranose-2,3,5-triacetate in the presence of a base to produce 1-O-benzyl-&bgr;-D-ribofuranose or an optical isomer thereof.

  本发明提供了一种高效生产&bgr;-D-核糖呋喃衍生物或其光学异构体的方法，该方法可用作制药核酸系列产品的合成中间体。该方法包括以下步骤：在酸催化剂的存在下，使&bgr;-D-核糖呋喃-1,2,3,5-四乙酸酯或其光学异构体与苯甲醇反应，以生产1-O-苄基-&bgr;-D-核糖呋喃-2,3,5-三乙酸酯或其光学异构体；在碱的存在下水解所得的1-O-苄基-&bgr;-D-核糖呋喃-2,3,5-三乙酸酯，以生产1-O-苄基-&bgr;-D-核糖呋喃或其光学异构体。
• Novel polysaccharides novel macromolecular conjugates of the polysaccharides
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0320942A2

  公开（公告）日：1989-06-21

  Synthesis of oligomeric subunits of the poly(ribosyl-ribitol-phosphate) capsular polysaccharide found on Haemophilus influenzae type b bacteria. The covalent attachment of these compounds to immunogenic proteins without using spacer elements.

  合成在 b 型流感嗜血杆菌上发现的聚（核糖核糖醇磷酸酯）荚膜多糖的低聚物亚基。在不使用间隔元件的情况下，将这些化合物共价连接到免疫原蛋白上。
• Purinyl and pyrimidinyl tetrahydrofurans
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0394893A2

  公开（公告）日：1990-10-31

  Antiviral activity is exhibited by compounds having the formula and pharmaceutically acceptable salts thereof wherein R1 is a purine or pyrimidine base or an analog thereof and R2 and R3 are independently hydrogen, -PO3H2 or - -X7, wherein X7 is hydrogen, alkyl, substituted alkyl or aryl.

  具有以下式子的化合物具有抗病毒活性 及其药学上可接受的盐类，其中 R1 是嘌呤或嘧啶碱或其类似物，R2 和 R3 独立地是氢、-PO3H2 或 -X7，其中 X7 是氢、烷基、取代的烷基或芳基。