2-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)oxy]pyridine | 1167997-28-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)oxy]pyridine
• 英文别名: [(2S,3S,4R,5R,6S)-4,5-diacetyloxy-2-methyl-6-pyridin-2-yloxyoxan-3-yl] acetate
• CAS: 1167997-28-5
• 化学式: C₁₇H₂₁NO₈
• 分子量: 367.356
• InChiKey: MSKNYTBHQJXUOD-KNKFVVRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 2-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)oxy]pyridine 在 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以91%的产率得到methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  2-Pyridyl glycoside: an alternative glycosyl donor in preactivation protocol

  摘要：

  2-Pyridyl glycosides have been identified to be powerful glycosyl donors for the preactivation-based oligosaccharide synthesis. By using stoichiometric amount of Tf2O, the 2-pyridyl glycosides were pre-activated, which subsequently underwent glycosylation reactions smoothly to produce the coupled products in high yields. Furthermore, the 2-pyridyl glycosides were applied to the efficient oligosaccharide assembly by the preactivation-based one-pot oligosaccharide synthesis protocol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.066
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide 、 2-羟基吡啶银盐 以 甲苯 为溶剂， 反应 1.0h， 以52%的产率得到2-[(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)oxy]pyridine
  参考文献：
  名称：

  2-Pyridyl glycoside: an alternative glycosyl donor in preactivation protocol

  摘要：

  2-Pyridyl glycosides have been identified to be powerful glycosyl donors for the preactivation-based oligosaccharide synthesis. By using stoichiometric amount of Tf2O, the 2-pyridyl glycosides were pre-activated, which subsequently underwent glycosylation reactions smoothly to produce the coupled products in high yields. Furthermore, the 2-pyridyl glycosides were applied to the efficient oligosaccharide assembly by the preactivation-based one-pot oligosaccharide synthesis protocol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.066

文献信息

• An improved procedure for nucleoside synthesis using glycosyl trifluoroacetimidates as donors
  作者：Jinxi Liao、Jiansong Sun、Biao Yu

  DOI：10.1016/j.carres.2009.03.010

  日期：2009.5

  Using glycosyl trifluoroacetimidates as donors and nitromethane (or acetonitrile) as solvent, silylation and subsequent glycosylation were realized in a 'one-pot' procedure to provide the corresponding nucleosides derivatives in high yields.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.