6-(4-fluorophenyl)-3-pyridinyl 5-thio-β-D-xylopyranoside | 910648-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(4-fluorophenyl)-3-pyridinyl 5-thio-β-D-xylopyranoside
• 英文别名: (2R,3R,4S,5S)-2-[6-(4-fluorophenyl)pyridin-3-yl]oxythiane-3,4,5-triol
• CAS: 910648-94-1
• 化学式: C₁₆H₁₆FNO₄S
• 分子量: 337.372
• InChiKey: VUCBZPQAPNUOJE-QKPAOTATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside 、 4-氟苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 0.33h， 以46%的产率得到6-(4-fluorophenyl)-3-pyridinyl 5-thio-β-D-xylopyranoside
  参考文献：
  名称：

  Palladium-catalyzed C–C coupling: efficient preparation of new 5-thio-β-d-xylopyranosides as oral venous antithrombotic drugs

  摘要：

  First examples of a Suzuki and Stille cross-coupling reaction to prepare derivatives of pyridinyl 5-thio-beta-D-xylopyranosides are described. Some of these compounds are orally active in an animal model of venous thrombosis. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.050

文献信息

• Novel Compounds Derived From 5-Thioxylose And Their Use In Therapeutics
  申请人：Barberousse Veronique

  公开号：US20080293768A1

  公开（公告）日：2008-11-27

  The invention relates to novel 5-thioxylose compounds, preferably derivatives of the 5-thioxylopyranose type, to the process for their preparation and to their use as active principles of drugs intended especially for the treatment or prevention of thrombosis or cardiac insufficiency.

  这项发明涉及新颖的5-硫木糖化合物，优选为5-硫木糖吡喃糖类衍生物，以及它们的制备过程和它们作为药物活性成分的用途，主要用于治疗或预防血栓形成或心脏功能不全。
• NOUVEAUX COMPOSES DERIVES DU 5-THIOXYLOSE ET LEUR UTILISATION THERAPEUTIQUE
  申请人：LABORATOIRES FOURNIER S.A.

  公开号：EP1861411A2

  公开（公告）日：2007-12-05
• US8148407B2
  申请人：——

  公开号：US8148407B2

  公开（公告）日：2012-04-03
• [EN] NOVEL COMPOUNDS DERIVED FROM 5-THIOXYLOSE AND THERAPEUTIC USE THEREOF<br/>[FR] NOUVEAUX COMPOSES DERIVES DU 5-THIOXYLOSE ET LEUR UTILISATION THERAPEUTIQUE
  申请人：FOURNIER LAB SA

  公开号：WO2006100413A2

  公开（公告）日：2006-09-28

  (EN) The invention relates to novel compounds derived from 5-thioxylose, preferably 5-thioxylopyranose-type derivatives, and to the preparation method thereof and the use of same as an active principle in medicaments which are intended, for example, for the treatment or prevention of thromboses or heart failure.(FR) L'invention concerne de nouveaux composés du 5-thioxylose, préférentiellement des dérivés de type 5-thioxylopyranose, ainsi que leur procédé de préparation et leur utilisation en tant que principe actif de médicaments, notamment destinés au traitement ou à la prévention des thromboses ou de l'insuffisance cardiaque.
• Palladium-catalyzed C–C coupling: efficient preparation of new 5-thio-β-d-xylopyranosides as oral venous antithrombotic drugs
  作者：M. Bondoux、L. Mignon、K. Ou、P. Renaut、D. Thomas、V. Barberousse

  DOI：10.1016/j.tetlet.2009.04.050

  日期：2009.7

  First examples of a Suzuki and Stille cross-coupling reaction to prepare derivatives of pyridinyl 5-thio-beta-D-xylopyranosides are described. Some of these compounds are orally active in an animal model of venous thrombosis. (c) 2009 Elsevier Ltd. All rights reserved.