allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside | 201043-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside
• 英文别名: (2S,3S,4aR,7S,8R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-prop-2-enoxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-8-ol
• CAS: 201043-07-4
• 化学式: C₁₄H₂₄O₇
• 分子量: 304.34
• InChiKey: ARMGQPQRXLRILK-BSOLPCOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.5h， 生成 2-(trityloxy)ethyl 3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-xylopyranoside
  参考文献：
  名称：

  第二信使肌醇1,4,5-三磷酸酯的模仿物（2-羟乙基）2-脱氧-α-D-苏-吡喃糖苷3,4,2'-三磷酸酯的合成及生物学评价

  摘要：

  （2-羟基乙基）2-脱氧-α-D-苏-戊吡喃糖苷3,4,2'-三磷酸（3）是从烯丙基-α-D-吡喃吡喃糖苷开始制备的。使用亚磷酰胺方法将通过明智的选择性保护和脱保护而获得的适当保护的2-脱氧中间体进行了磷酸化。最终的去保护了预期模拟肌肌醇1,4,5-三磷酸。

  DOI：

  10.1080/07328309908544031
• 作为产物：
  描述：

  D-吡喃木糖 在 camphor-10-sulfonic acid 、 乙酰氯 、 原甲酸三甲酯 作用下， 以 甲醇 为溶剂， 反应 17.83h， 生成 allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside
  参考文献：
  名称：

  Jenkins, David J.; Potter, Barry V. L., Journal of the Chemical Society. Perkin transactions I, 1998, # 1, p. 41 - 50

  摘要：

  DOI：

文献信息

• 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.