methyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 1309666-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-glucopyranoside；methyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside
• CAS: 1309666-32-7
• 化学式: C₆₂H₅₈O₁₅
• 分子量: 1043.13
• InChiKey: MUIHRXLDCLCKEB-PRWIROASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.39
• 重原子数：
  77.0
• 可旋转键数：
  22.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  169.81
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide 在 18-冠醚-6 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 20.0h， 生成 methyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  S-苯并咪唑基糖苷作为活性-潜在策略合成寡糖的平台

  摘要：

  开展业务：S-苯并咪唑基 (SBiz) 异头部分是一种新的离去基团，可以在多种条件下被激活进行糖基化，包括金属辅助和烷基化途径。应用取代的 SBiz 部分（X=苯甲酰基，见图）可实现活性-潜在和武装-解除武装类型的寡糖组装。

  DOI：

  10.1002/anie.201007212

文献信息

• <i>O</i>-Glycosylation Enabled by <i>N-</i>(Glycosyloxy)acetamides
  作者：Miao Liu、Bo-Han Li、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1021/acs.joc.8b01003

  日期：2018.8.3

  A novel glycosylation protocol has been established by using N-(glycosyloxy)acetamides as glycosyl donors. The N-oxyacetamide leaving group in donors could be rapidly activated in the presence of Cu(OTf)2 or SnCl4 under microwave irradiation. This glycosylation process afforded the coupled products in high yields, and the reaction enjoyed a broad substrate scope, even for disarmed donors and hindered

  通过使用N-（糖基氧基）乙酰胺作为糖基供体已经建立了新的糖基化方案。在微波辐射下，存在Cu（OTf）2或SnCl 4的情况下，供体中的N-氧乙酰胺离去基团可以快速活化。该糖基化过程以高收率提供了偶联产物，并且该反应享有广泛的底物范围，即使对于缴械的供体和受阻的受体也是如此。供体的容易获得，N-（糖基氧基）乙酰胺的高稳定性以及小的离去基团使该方法非常实用。
• A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide–Triflic Acid Catalysis
  作者：Scott A. Geringer、Yashapal Singh、Daniel J. Hoard、Alexei V. Demchenko

  DOI：10.1002/chem.201905576

  日期：2020.6.26

  Following our discovery that silver(I) oxide‐promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, we report herein a new discovery that glycosyl chlorides are even more effective glycosyl donors under these reaction conditions. The developed reaction conditions work well with a variety of glycosyl chlorides. Both benzoylated and benzylated

  我们发现在催化TMSOTf或TfOH的存在下，氧化银（I）促进的糖基溴化物的糖基化作用可以大大加速，我们在此报告了一个新发现，即在这些反应条件下糖基氯化物是更有效的糖基供体。发达的反应条件适用于各种糖基氯化物。苯甲酰化氯和苄基化氯化物均已成功糖基化，这些反应条件被证明对偶联含有氮和硫原子的底物有效。这种糖基化的另一个便利特征是可以直观地监测反应的进程。它的完成可以通过Ag 2 O特有的深色消失来判断。
• Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation
  作者：Tinghua Wang、Yashapal Singh、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1002/ejoc.201801272

  日期：2018.12.19

  Glycosyl nitrates are important synthetic intermediates in the synthesis of 2-amino sugars, 1,2-orthoesters or, more recently, 2-OH glucose. However, glycosyl nitrates have never been glycosidated. Presented herein is our first attempt to use glycosyl nitrates as glycosyl donors for O-glycosylation. Lanthanide triflates showed good affinity to activate the nitrate leaving group.

  硝酸糖基是合成 2-氨基糖、1,2-原酸酯或最近的 2-OH 葡萄糖的重要合成中间体。然而，硝酸糖基从未被糖苷化。本文介绍的是我们首次尝试使用硝酸糖基作为 O-糖基化的糖基供体。镧系三氟甲磺酸盐对激活硝酸盐离去基团显示出良好的亲和力。
• N‐Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile
  作者：Ganesh Shrestha、Matteo Panza、Yashapal Singh、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1002/ejoc.202200300

  日期：2022.5.13

  Protecting the nitrogen atom in the S-indolyl leaving group of glycosyl donors helped to reduce the amount of NIS/TfOH required for their activation in glycosylation. The activation with silver salts shifted from the remote to the direct activation pathway offering additional insight into the reaction mechanism by which these leaving groups are activated.

  保护糖基供体的 S-吲哚基离去基团中的氮原子有助于减少糖基化激活所需的 NIS/TfOH 量。银盐的激活从远程激活途径转变为直接激活途径，从而提供了对这些离去基团被激活的反应机制的更多见解。