methyl 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 1233488-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl 6-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；methyl O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；[(2R,3S,4R,5R,6R)-3,4-dibenzoyloxy-5-(1,3-dioxoisoindol-2-yl)-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 1233488-75-9
• 化学式: C₆₃H₅₇NO₁₅
• 分子量: 1068.14
• InChiKey: ISLFLQGRIXFJNE-KZTMFSDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  79
• 可旋转键数：
  24
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  181
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  3,4,5-tri-O-benzoyl-2-deoxy-2-phthalimido-D-glucopyranose 在 氯化亚砜 、 silver(l) oxide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 methyl 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  通过使用氧化银（I）协同三氟乙酸催化高效糖基氯化物的糖基化。

  摘要：

  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。

  DOI：

  10.1002/chem.201905576

文献信息

• Glycosylation with Disarmed Glycosyl Bromides Promoted by Iodonium Ions
  作者：Gyrithe Lanz、Robert Madsen

  DOI：10.1002/ejoc.201600545

  日期：2016.6

  Iodonium ions have been developed for activating glycosyl bromides in the coupling to glycosyl acceptors. The iodonium ions are generated from N-iodosuccinimide and a protic acid such as camphorsulfonic acid or triflic acid, where the latter gives the most reactive promoter system. The couplings occur with the release of iodine monobromide, and the best results are obtained with benzoylated glycosyl

  碘鎓离子已被开发用于激活与糖基受体偶联的糖基溴化物。碘鎓离子由 N-碘代琥珀酰亚胺和质子酸（如樟脑磺酸或三氟甲磺酸）产生，其中后者提供最具反应性的促进剂系统。偶联随着一溴化碘的释放而发生，使用苯甲酰化糖基供体和受体获得最佳结果。通过这种方式，去武装的糖基溴化物可以作为糖基供体，而无需使用重金属盐。
• Comparison of the Armed/Disarmed Building Blocks of the <scp>d</scp>-Gluco and <scp>d</scp>-Glucosamino Series in the Context of Chemoselective Oligosaccharide Synthesis
  作者：Teerada Kamkhachorn、Archana R. Parameswar、Alexei V. Demchenko

  DOI：10.1021/ol101089u

  日期：2010.7.2

  A very elegant Fraser-Reid armed-disarmed approach recently expanded to the building blocks of the superarmed and superdisarmed series shows very high utility in chemoselective oligosaccharide synthesis. Although a number of studies dedicated to the chemoselective activation of 2-amino-2-deoxysugars have emerged, little remains known about how the reactivity of the armed/disarmed building blocks of the neutral sugars directly compares to that of their 2-aminosugar counterparts. A preliminary study of this comparative reactivity is presented.
• 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。