allyl 3,4-di-O-benzoyl-2-O-benzyl-α-D-xylopyranoside | 196859-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,4-di-O-benzoyl-2-O-benzyl-α-D-xylopyranoside
• 英文别名: [(3R,4S,5R,6S)-4-benzoyloxy-5-phenylmethoxy-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 196859-39-9
• 化学式: C₂₉H₂₈O₇
• 分子量: 488.537
• InChiKey: INFBBIULXZWICG-KGWIZABPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 3,4-di-O-benzoyl-2-O-benzyl-α-D-xylopyranoside 在 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 sodium hydride 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 6.5h， 生成 [(2R)-[2-hydroxy-3-(6-amino-9H-purin-9-yl)]propyl] 2-O-benzyl-3,4-di-O-benzoyl-α-D-xylopyranoside
  参考文献：
  名称：

  d-myo-Inositol-1,4,5-trisphosphate and Adenophostin Mimics: Importance of the Spatial Orientation of a Phosphate Group on the Biological Activity

  摘要：

  Three different routes for the synthesis of heterocyclic analogues of the second messenger D-myo-inositol-1,4,5-trisphosphate (InsP(3)) and the natural adenophostins. starting from allyl D-xyloside are described. The two diastereoisomers at C-2 of new compounds. which we named xylophostins, were obtained. The preliminary biological studies shows that the presence of the adenine residue has a beneficial effect on the affinity for the receptor. The low potency of one of the two diastereoisomeric compounds shows that the configuration of the carbon bearing the non-vicinal phosphate group is an important requirement for a high affinity to the receptor. These results provide evidence for the existence of a binding pocket for the adenine ring nearby the InsP(3) binding site. The consequence of these stabilizing interactions should be to place the phosphate group in a suitable position to perfectly mimic InsP(3) in the more active diastereoisomer. Obviously, in the other diastereoisomer, the phosphate cannot accommodate the same orientation, thus explaining the low affinity. The existence of such a binding pocket for adenine is in line with the high potency of adenophostins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00329-7
• 作为产物：
  描述：

  苯甲酰氯 、 allyl 2-O-benzyl-α-D-xylopyranoside 在 吡啶 作用下， 反应 16.0h， 以81%的产率得到allyl 3,4-di-O-benzoyl-2-O-benzyl-α-D-xylopyranoside
  参考文献：
  名称：

  Moitessier, Nicolas; Maigret, Bernard; Chretien, Francoise, European Journal of Organic Chemistry, 2000, # 6, p. 995 - 1005

  摘要：

  DOI：

文献信息

• Moitessier, Nicolas; Maigret, Bernard; Chretien, Francoise, European Journal of Organic Chemistry, 2000, # 6, p. 995 - 1005
  作者：Moitessier, Nicolas、Maigret, Bernard、Chretien, Francoise、Chapleur, Yves

  DOI：——

  日期：——
• d-myo-Inositol-1,4,5-trisphosphate and Adenophostin Mimics: Importance of the Spatial Orientation of a Phosphate Group on the Biological Activity
  作者：Fabien Roussel、Nicolas Moitessier、Mauricette Hilly、Françoise Chrétien、Jean-Pierre Mauger、Yves Chapleur

  DOI：10.1016/s0968-0896(01)00329-7

  日期：2002.3

  Three different routes for the synthesis of heterocyclic analogues of the second messenger D-myo-inositol-1,4,5-trisphosphate (InsP(3)) and the natural adenophostins. starting from allyl D-xyloside are described. The two diastereoisomers at C-2 of new compounds. which we named xylophostins, were obtained. The preliminary biological studies shows that the presence of the adenine residue has a beneficial effect on the affinity for the receptor. The low potency of one of the two diastereoisomeric compounds shows that the configuration of the carbon bearing the non-vicinal phosphate group is an important requirement for a high affinity to the receptor. These results provide evidence for the existence of a binding pocket for the adenine ring nearby the InsP(3) binding site. The consequence of these stabilizing interactions should be to place the phosphate group in a suitable position to perfectly mimic InsP(3) in the more active diastereoisomer. Obviously, in the other diastereoisomer, the phosphate cannot accommodate the same orientation, thus explaining the low affinity. The existence of such a binding pocket for adenine is in line with the high potency of adenophostins. (C) 2002 Elsevier Science Ltd. All rights reserved.