phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside | 1381857-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside
• 英文别名: phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside
• CAS: 1381857-96-0
• 化学式: C₆₂H₅₈O₁₄S
• 分子量: 1059.2
• InChiKey: KLVASKJUGSOFIE-HYAOFUCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.24
• 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：
  160.58
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 、 phenyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside 在 1-(p-tolylthio)azepan-2-one 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以94%的产率得到phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf

  摘要：

  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.

  DOI：

  10.1016/j.carres.2012.03.024

文献信息

• Iron(<scp>iii</scp>) chloride modulated selective 1,2-trans glycosylation based on glycosyl trichloroacetimidate donors and its application in orthogonal glycosylation
  作者：Mana Mohan Mukherjee、Nabamita Basu、Rina Ghosh

  DOI：10.1039/c6ra21859h

  日期：——

  FeCl3 can also modulate the 1,2-trans selectivity of the reaction of 2-O-alkylated gluco- and galacto-pyranosyl trichloroacetimidates with phenolic compounds leading to the generation of the corresponding β-O-aryl glycosides in excellent yield and selectivity. Apart from these the present methodology has been successfully utilized for double glycosylation and orthogonal glycosylation reactions along

  人们已经集中研究了一种新的糖基化方法，该方法可从10摩尔％的FeCl 3介导的相应的三氯乙酰亚氨酸酯供体有效立体选择性合成β-葡萄糖和半乳糖苷。FeCl 3也已应用于许多基于葡萄糖，半乳糖，甘露糖和鼠李糖的三氯乙酰亚氨酸酯供体，这些供体在C-2位置掺入了各种保护基，从而制备了多种具有优异的1,2-反式选择性的二糖和三糖。FeCl 3还可调节2- O反应的1,2-反式选择性-烷基化的葡糖基和半乳糖基-吡喃糖基三氯乙酰亚胺酸酯与酚类化合物的结合，可导致以优异的产率和选择性生成相应的β- O-芳基糖苷。除此之外，本方法已成功地用于双糖基化和正交糖基化反应，以及在三锅合成的一锅三组分正交糖基化反应中的应用。