2-biphenylmethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 1093186-53-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-biphenylmethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS: 1093186-53-8
• 化学式: C₂₇H₃₀O₁₀
• 分子量: 514.529
• InChiKey: VBVQIZVSWFODRK-IURCNINISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-biphenylmethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 氨 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以105 mg的产率得到2-biphenylmethyl β-D-glucopyranoside
  参考文献：
  名称：

  Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases

  摘要：

  Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1 -> 3)-beta-D-Glcp and aryl beta-D-Glcp-(1 -> 3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-D-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1 -> 3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.018
• 作为产物：
  描述：

  2-联苯基甲醇 、 2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以31%的产率得到2-biphenylmethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases

  摘要：

  Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1 -> 3)-beta-D-Glcp and aryl beta-D-Glcp-(1 -> 3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-D-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1 -> 3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.018