methyl 3-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranoside | 1340482-50-9

• 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: methyl 3-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranoside
• CAS: 1340482-50-9
• 化学式: C₅₇H₅₈O₁₅Si
• 分子量: 1011.16
• InChiKey: RRJKHKKUXRQRTE-CPIJBRKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  73.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  191.81
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以18%的产率得到methyl 2-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-(6-O-tert-butyldiphenylsilyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Directing/protecting groups mediate highly regioselective glycosylation of monoprotected acceptors

  摘要：

  A directing/protecting group designed for regioselective functionalization of partially-protected glucopyrannosides has been successfully used to prepare disaccharides in high yields. Most importantly, it has been demonstrated that highly regioselective and stereoselective glycosylation can be achieved when disarmed donors are employed. This study demonstrates the ability of directing/protecting group to induce regioselective glycosylation of carbohydrates and opens the field to the design of other DPGs for other monosaccharides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.026