allyl 2-O-benzyl-α-D-xylopyranoside | 172795-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-benzyl-α-D-xylopyranoside
• 英文别名: (3R,4S,5R,6S)-5-phenylmethoxy-6-prop-2-enoxyoxane-3,4-diol
• CAS: 172795-17-4
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: JPKKBFLWQJIREO-BARDWOONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 2-O-benzyl-α-D-xylopyranoside 在 吡啶 、 水 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 叔丁醇 为溶剂， 反应 16.0h， 生成 (2,3-dihydroxypropyl) 2-O-benzyl-3,4-O-cyclohexanecarbonyl-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：
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 Dowex 50W H⁽¹⁺⁾ 、 sodium methylate 、 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 55.0h， 生成 allyl 2-O-benzyl-α-D-xylopyranoside
  参考文献：
  名称：

  Synthesis and biological activities of inositol 1,4,5-trisphosphate mimics related to xylopyranosides

  摘要：

  2', 3, 4-trisphosphates of (2-hydroxyethyl) alpha- and beta-D-xylopyranosides and 3', 3, 4-trisphosphates of (3-hydroxypropyl) alpha- and beta-D-xylopyranosides have been prepared from allyl-D-xylosides and showed agonistic properties toward inositol 1, 4, 5-trisphosphate receptor.

  DOI：

  10.1016/0040-4039(95)01677-a

文献信息

• New Sugar‐Based Permeant Analogs of D‐ Myo ‐Inositol 1,4,5‐Trisphosphate Mimicking the Effect of Vasopressin: Synthesis and Biologic Evaluation*
  作者：Françoise Chrétien、Fabien Roussel、Mauricette Hilly、Jean‐Pierre Mauger、Yves Chapleur

  DOI：10.1081/car-200068070

  日期：2005.8.1

  of the xylose‐inositol analogy, a series of permeant analogs of D‐myo‐inositol 1,4,5‐trisphosphate (InsP3) have been synthesized by various esterifications of the phosphate groups. Their ability to cross the cell membrane has been tested on vasopressin cells. Very fast liberation of calcium occurs when active analogs are introduced in the extracellular medium on intact cells. Membrane crossing as well

  根据木糖-肌醇的类似物，已通过磷酸酯基团的各种酯化反应合成了一系列D-肌醇1,4,5-三磷酸酯（InsP3）的渗透性类似物。在血管加压素细胞上已经测试了它们穿过细胞膜的能力。当将活性类似物引入完整细胞的细胞外培养基中时，钙会非常快速地释放出来。使用所有磷酸酯基团的酰氧基甲基酯化，膜的转运以及磷酸酯的水解都非常快。游离化合物在细胞中的行为类似于InsP3。对于表达血管加压素受体的大鼠肝细胞，以这种方式制备的一种类似物的行为类似于血管加压素。*致敬Jacques H. van Boom及其在该领域的杰出贡献。
• Design, synthesis and preliminary biological evaluation of a focused combinatorial library of stereodiverse carbohydrate-scaffold-based peptidomimetics
  作者：Nicolas Moitessier、Sylvie Dufour、Françoise Chrétien、Jean Paul Thiery、Bernard Maigret、Yves Chapleur

  DOI：10.1016/s0968-0896(00)00256-x

  日期：2001.2

  A focused combinatorial library of 126 mimetics of the RGD sequence based on sugar scaffolds have been rationally constructed using molecular modeling, with a particular emphasis on the stereodiversity of the library. A liquid phase, mix and divide synthesis was used, active compounds being identified by using orthogonal libraries and recursive deconvolution strategies.

  已使用分子模型合理构建了基于糖支架的RGD序列的126个模拟物的聚焦组合文库，并特别强调了该文库的立体多样性。使用液相，混合和分开合成，通过使用正交文库和递归解卷积策略鉴定活性化合物。
• Jenkins, David J.; Potter, Barry V. L., Journal of the Chemical Society. Perkin transactions I, 1998, # 1, p. 41 - 50
  作者：Jenkins, David J.、Potter, Barry V. L.

  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.
• Xylopyranoside-based agonists of d-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity
  作者：Heidi J. Rosenberg、Andrew M. Riley、Rachel D. Marwood、Vanessa Correa、Colin W. Taylor、Barry V.L. Potter

  DOI：10.1016/s0008-6215(01)00067-2

  日期：2001.5

  The synthesis of a series of tetrahydrofuranyl alpha- and beta -xylopyranoside trisphosphates, designed by excision of three motifs of adenophostin A is reported. The synthetic route features improved preparations of allyl alpha -D-xylopyranoside and its 2-O-benzyl ether, and gives access to four diastereoisomeric trisphosphates, which show a range of abilities to mobilise Ca2+ from the intracellular stores of hepatocytes. A comparison of the potencies of the four trisphosphates provides useful information relating to the effects of stereochemical variation on the recognition of carbohydrate-based trisphosphates by D-myo-inositol 1,4,5-trisphosphate receptors. 1-O-[(3 'S,4 'R)-3-hydroxytetrahydrofuran-4-yl] alpha -D-xylopyranoside 3,4,3 ' -trisphosphate (8) is the most active member of the series with a potency close to Ins(1,4,5)P-3; a beta -linked analogue, 1-O-[(3 'R,4 'S)-3-hydroxytetrahydrofuran-4-yl] beta -D-xylopranoside 3,4,3 ' -trisphosphate, is ca. 20-fold weaker than Ins(1,4,5)P-3, and the other compounds are much less active. While no compound attained a potency close to that of adenophostin A, we believe that 8 represents the minimal structure for potent Ca2+-releasing activity in this type of carbohydrate-based analogue. (C) 2001 Elsevier Science I,td. All rights reserved.