octyl 6-O-[6-(2-pyridin-2-ylethyl)-pyridin-2-yl-di-p-tolylmethyl]-β-D-glucopyranoside | 1340482-46-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 6-O-[6-(2-pyridin-2-ylethyl)-pyridin-2-yl-di-p-tolylmethyl]-β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-[[bis(4-methylphenyl)-[6-(2-pyridin-2-ylethyl)pyridin-2-yl]methoxy]methyl]-6-octoxyoxane-3,4,5-triol
• CAS: 1340482-46-3
• 化学式: C₄₁H₅₂N₂O₆
• 分子量: 668.874
• InChiKey: HPEJZYXZYARLCE-HRSAFRLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  octyl 6-O-[6-(2-pyridin-2-ylethyl)-pyridin-2-yl-di-p-tolylmethyl]-β-D-glucopyranoside 、 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87%的产率得到octyl 3-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-6-O-[6-(2-pyridin-2-ylethyl)-pyridin-2-yl-di-p-tolylmethyl]-β-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
• 作为产物：
  描述：

  octyl 2,3,4-tri-O-acetyl-6-O-[6-(2-pyridin-2-ylethyl)-pyridin-2-yl-di-p-tolylmethyl]-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到octyl 6-O-[6-(2-pyridin-2-ylethyl)-pyridin-2-yl-di-p-tolylmethyl]-β-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

文献信息

• Directing/protecting groups mediate highly regioselective glycosylation of monoprotected acceptors
  作者：Janice Lawandi、Sylvain Rocheleau、Nicolas Moitessier

  DOI：10.1016/j.tet.2011.07.026

  日期：2011.10

  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.