Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester | 241129-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester
• 英文别名: methyl 2,4,6-tri-O-acetyl-3-O-benzyl-α-L-idopyranoside
• CAS: 241129-72-6
• 化学式: C₂₀H₂₆O₉
• 分子量: 410.421
• InChiKey: DQKIXWPNUCSKEQ-PXTPFGJHSA-N

物化性质

• 沸点：
  489.348±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.241±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester 在 吡啶 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 水 、 sodium methylate 、 2,2-二甲氧基丙烷 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranoside
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9
• 作为产物：
  描述：

  [(2S,3R,4S,5R)-3,5-diacetyloxy-6-hydroxy-4-phenylmethoxyoxan-2-yl]methyl acetate 在 三氟化硼乙醚 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

  摘要：

  A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1-->4)-2-O-sulfo-alpha-L-idopyranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited (3)H-Iabelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01084-9

文献信息

• Glycosylations of Simple Acceptors with 2‐ <i>O</i> ‐Acyl <scp>l</scp> ‐Idose or <scp>l</scp> ‐Iduronic Acid Donors Reveal Only a Minor Role for Neighbouring‐Group Participation
  作者：Shifaza Mohamed、Qi Qi He、Romain J. Lepage、Elizabeth H. Krenske、Vito Ferro

  DOI：10.1002/ejoc.201800318

  日期：2018.5.24

  Several l-idose and l-iduronic acid glycosyl donors (mostly thioglycosides but also halides and trichloroacetimidates) with acyl protecting groups at the C-2 position were prepared and evaluated in glycosylation reactions with simple acceptors. In glycosaminoglycan oligosaccharide syntheses in the literature, the presence of C-2 acyl protecting groups in l-ido-configured glycosyl donors generally results

  在 C-2 位具有酰基保护基团的几个 l-艾杜糖和 l-艾杜糖醛酸糖基供体（主要是硫代糖苷，但也有卤化物和三氯乙酰亚胺）被制备并在与简单受体的糖基化反应中进行评估。在文献中的糖胺聚糖寡糖合成中，l-ido 构型糖基供体中 C-2 酰基保护基团的存在通常导致 1,2-反式糖苷键的排他性形成，这一发现通常归因于相邻基团参与。然而，这里报道的具有 l-ido 配置的供体（特别是硫糖苷）的简单醇的糖基化通常显示出不完全的立体控制并产生 1,2-反式和 1,2-顺式产物的混合物，表明相邻组的参与具有在这些反应中不太重要。确定了糖基供体和反应条件，它们对作为主要产物的所需 α-1-异头异构体（1,2-反式）提供了改进的选择性，但不是唯一的。有趣的是，在相同反应条件下，使用更复杂的单糖受体进行糖基化仅产生预期的 1,2-反式产物。使用密度泛函理论 (DFT) 计算探索了相邻基团参与这些糖基化的作用，这表