methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside | 1256155-25-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside；methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside；Bn(-2)Glc3Ac4Ac6Ac(a1-3)[Bn(-2)][Bn(-4)][Bn(-6)]a-Glc1Me；[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-[(2S,3R,4S,5R,6R)-2-methoxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 1256155-25-5
• 化学式: C₄₇H₅₄O₁₄
• 分子量: 842.937
• InChiKey: KSAHSKPQUKJXOB-FITGBFLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  61
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  ethyl-3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-D-glucopyranoside 在 溴 、 silver(l) oxide 、 3,3-二氟-1,3-二氢-2H-吲哚-2-酮 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  再生糖基化

  摘要：

  以前，我们交流了3,3-二氟吲哚（HOFox）介导的糖基化作用，其中3,3-二氟-3 H-吲哚-2-基（OFox）酰亚胺化被发现是关键中间体。从相应的糖基溴化物的原位合成和OFox酰亚胺化物的活化都可以以再生方式进行。在这里，我们将这项研究扩展到使用不同糖系列合成各种糖苷键。这项研究的主要结果涉及糖基化的产率提高和/或反应时间减少。在没有反应性的糖基供体和/或糖基受体的情况下，HOFox介导的反应的作用特别明显。还报道了寡糖的多步骤再生合成。

  DOI：

  10.1021/acs.joc.7b02768

文献信息

• 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。
• On the stereoselectivity of glycosidation of thiocyanates, thioimidates, and thioglycosides
  作者：Sophon Kaeothip、Steven J. Akins、Alexei V. Demchenko

  DOI：10.1016/j.carres.2010.08.003

  日期：2010.10

  Comparative side-by-side glycosylation studies demonstrated that glycosyl thiocyanates, thioimidates, and thioglycosides provide comparative stereoselectivities in glycosylations. Very high alpha-stereoselectivity that was previously recorded for glycosyl thiocyanates can be achieved, but only if glycosyl acceptors are equipped with electron-withdrawing acyl substituents. Partially benzylated glycosyl acceptors provided relatively modest stereoselectivity, which was on a par with other common glycosyl donors. Accordingly, thioimidates and thioglycosides showed high stereoselectivity similarly to that of thiocyanates with different classes of acylated primary and secondary glycosyl acceptors. (C) 2010 Elsevier Ltd. All rights reserved.