p-methylphenyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside | 1363157-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside
• CAS: 1363157-90-7
• 化学式: C₆₂H₅₇NO₁₂S
• 分子量: 1040.2
• InChiKey: WVNOSQGXSWHDFM-UTKKPSPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.31
• 重原子数：
  76.0
• 可旋转键数：
  18.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  137.52
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 、 p-methylphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以30%的产率得到p-methylphenyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Acyl and Silyl Group Effects in Reactivity-Based One-Pot Glycosylation: Synthesis of Embryonic Stem Cell Surface Carbohydrates Lc₄ and IV²Fuc-Lc₄

  摘要：

  Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts. These findings were applied in reactivity-based one-pot assembly of linker-attached Lc(4) and IV(2)Fuc-Lc(4), which are components of human embryonic stem cell surface. The sugar-galectin-1 binding was also examined.

  DOI：

  10.1021/ja300284x