4-(benzoyl)phenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside | 147029-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(benzoyl)phenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
• 英文别名: [(3R,4S,5R,6S)-4,5-diacetyloxy-6-(4-benzoylphenoxy)oxan-3-yl] acetate
• CAS: 147029-58-1
• 化学式: C₂₄H₂₄O₉
• 分子量: 456.449
• InChiKey: HHHVSQLBTWLPFZ-ONTLXTELSA-N

物化性质

• 沸点：
  559.2±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(benzoyl)phenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 sodium tetrahydroborate 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2S,3R,4S,5R)-2-(4-Benzyl-phenoxy)-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Glycosylated derivatives of benzophenone, benzhydrol and benzhydril as potential venous antithrombotic agents

  摘要：

  A series of glycosylated derivatives of benzophenone, benzhydrol, and benzhydril has been synthesized and evaluated for potential activity as venous antithrombotic agents. Studies on structure-activity relationships revealed that compounds having an electron-withdrawing group in the benzhydril or benzhydrol moiety, and specifically those having the beta-D-xylopyranosyl structure in the sugar moiety, were good antithrombotic agents in a rat model of venous thrombosis.

  DOI：

  10.1021/jm00059a015
• 作为产物：
  描述：

  4-羟基-二苯甲酮 、 2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 silver(l) oxide 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以30%的产率得到4-(benzoyl)phenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Glycosylated derivatives of benzophenone, benzhydrol and benzhydril as potential venous antithrombotic agents

  摘要：

  A series of glycosylated derivatives of benzophenone, benzhydrol, and benzhydril has been synthesized and evaluated for potential activity as venous antithrombotic agents. Studies on structure-activity relationships revealed that compounds having an electron-withdrawing group in the benzhydril or benzhydrol moiety, and specifically those having the beta-D-xylopyranosyl structure in the sugar moiety, were good antithrombotic agents in a rat model of venous thrombosis.

  DOI：

  10.1021/jm00059a015

文献信息

• Benzylphenyl osides, method of preparation and use therefor
  申请人：Societe de Recheres Industrielles

  公开号：US04598068A1

  公开（公告）日：1986-07-01

  The present invention relates, by way of new industrial products, to the benzylphenyl osides of the formula ##STR1## in which: X.sub.1, X.sub.2, X.sub.3, X.sub.4 and X.sub.5, which are identical or different, each represent a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkyl group substituted by one or more halogen atoms (in particular a CF.sub.3 group), an OH group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkoxy group substituted by one or more halogen atoms, a nitro group, a group NR'R" (in which R' and R", which are identical or different, each represent the hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or an acetyl group), a methylthio group, a methylsulfinyl group or a mesyl group, and R represents an ose radical chosen from the group comprising (a) the .alpha.-L-rhamnosyl radical, (b) non-hydrolyzable monosaccharide radicals and (c) non-hydrolyzable monosaccharide radicals in which the hydroxyl group on the carbon atom in the 2-position is replaced with an amine group, the hydroxyl and amine groups of the group R being capable of acetylation, and their addition salts in cases where at least one of the groups X.sub.1, X.sub.2, X.sub.3, X.sub.4, X.sub.5 and R comprises a basic radical. These new products are useful in therapy. They can be prepared by reducing the corresponding benzoylphenyl and .alpha.-hydroxybenzylphenyl osides.

  本发明涉及新的工业产品，具体为公式 ##STR1## 中的苯甲基苯基醚，其中：X.sub.1、X.sub.2、X.sub.3、X.sub.4和X.sub.5，它们相同或不同，分别代表氢原子、卤素原子、C.sub.1-C.sub.4烷基、被一个或多个卤素原子（特别是CF.sub.3基团）取代的C.sub.1-C.sub.4烷基、OH基、C.sub.1-C.sub.4烷氧基、被一个或多个卤素原子取代的C.sub.1-C.sub.4烷氧基、硝基、NR'R"基团（其中R'和R"相同或不同，分别代表氢原子、C.sub.1-C.sub.4烷基或乙酰基）、甲硫基、甲磺酰基或甘氨酸基，而R代表从羟基乙醇中选择的ose基团，包括（a）.alpha.-L-鼠李糖基团，（b）不可水解的单糖基团和（c）不可水解的单糖基团，其中2-位上的碳原子的羟基被氨基取代，羟基和氨基基团可以乙酰化，在至少有一个基团X.sub.1、X.sub.2、X.sub.3、X.sub.4、X.sub.5和R包含碱性基团的情况下，还包括它们的加成盐。这些新产品在治疗中很有用。它们可以通过还原相应的苯甲酰苯基和.alpha.-羟基苯甲基苯基醚来制备。
• Benzyl-phényl-osides, procédé de préparation et utilisation
  申请人：FOURNIER INNOVATION ET SYNERGIE

  公开号：EP0133103B1

  公开（公告）日：1987-11-11
• US4598068A
  申请人：——

  公开号：US4598068A

  公开（公告）日：1986-07-01