1-O-methyl-2:3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-methyl-2:3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside
• 英文别名: methyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-4)[Bz(-2)][Bz(-3)][Bz(-6)]a-Glc1Me；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-methoxy-3-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• 化学式: C₆₂H₆₀O₁₄
• 分子量: 1029.15
• InChiKey: UDWRZJBERYQDND-OBCQBQLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  76
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 、 p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 在 六氢-1-(苯基硫代)-2H-氮杂卓-2-酮 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到1-O-methyl-2:3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  N-(Phenylthio)-ε-caprolactam:  A New Promoter for the Activation of Thioglycosides

  摘要：

  N-(Phenylthio)-epsilon-caprolactam (1) has been applied as a new promoter for the activation of thioglycosides. This proceeds by the reaction of 1 with trifluoromethansulfonic anhydride, which subsequently activates the thioglycoside for glycosidic bond formation. Notably, the reaction proceeds efficiently at room temperature and is adaptable to our reactivity-based one-pot oligosaccharide synthesis.

  DOI：

  10.1021/ol0400084

文献信息

• Fluoropyridyl Sugars – Masked Imidate Glycosyl Donors that Display Reactivity, Selectivity, and Stability
  作者：Ray Leslie、Kavnen Tseke、Agneta Vitkute、Sophie Benjamin、L. Seetohul

  DOI：10.1055/s-0036-1588478

  日期：2017.10

  from the corresponding glycosyl bromides, are shown to be excellent donors in glycosylation reactions. Both armed and disarmed donors were prepared and reacted smoothly with a series of glycosyl acceptors. Coupling proceeded in high yields, with activation of the donor achieved using a range of promoters, and also displayed unusually high selectivity. In addition these novel systems offer the potential

  由相应的糖基溴化物合成的氟吡啶基糖苷被证明是糖基化反应中的出色供体。准备好武装和解除武装的供体并与一系列糖基受体顺利反应。偶联以高产率进行，使用一系列启动子实现了供体的活化，并且还表现出异常高的选择性。此外，这些新系统提供了引入一系列具有“可调反应性”的糖基供体的潜力。
• <i>N</i>-(Phenylthio)-ε-caprolactam:  A New Promoter for the Activation of Thioglycosides
  作者：Sergio G. Durón、Tülay Polat、Chi-Huey Wong

  DOI：10.1021/ol0400084

  日期：2004.3.1

  N-(Phenylthio)-epsilon-caprolactam (1) has been applied as a new promoter for the activation of thioglycosides. This proceeds by the reaction of 1 with trifluoromethansulfonic anhydride, which subsequently activates the thioglycoside for glycosidic bond formation. Notably, the reaction proceeds efficiently at room temperature and is adaptable to our reactivity-based one-pot oligosaccharide synthesis.
• Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf
  作者：Sajal Kumar Maity、Nabamita Basu、Rina Ghosh

  DOI：10.1016/j.carres.2012.03.024

  日期：2012.6

  N-(p-Methylphenylthio)-epsilon-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both 'armed' and 'disarmed' thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot oligosaccharide assembly strategy. (C) 2012 Elsevier Ltd. All rights reserved.