methyl 2,3-di-O-benzyl-5,6-dideoxy-β-L-arabino-hex-5-yofuranoside | 1422008-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-5,6-dideoxy-β-L-arabino-hex-5-yofuranoside
• CAS: 1422008-01-2
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: LXKIFCMWUPMJNM-UWHLTILDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide 、 methyl 2,3-di-O-benzyl-5,6-dideoxy-β-L-arabino-hex-5-yofuranoside 在 diethylzinc 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 3.0h， 以91%的产率得到methyl 5,6-tetradehydro-5,6,7,10-tetradeoxy-7,10-hydroxylamino-2,3,8,9,11,12-hexa-O-benzyl-D-galacto-β-D-galacto-dodecafuranose
  参考文献：
  名称：

  Stereoselective synthesis of a novel Galf-disaccharide mimic: β-d-galactofuranosyl-(1-5)-β-d-galactofuranosyl motif of mycobacterial cell walls

  摘要：

  A Galf-disaccharide mimic, an analogue of the acceptor substrates of mycobacterial Galf-transferases, was obtained by nucleophilic addition of a L-arabinofurano-alkyne to iminogalactitol-derived nitrone. Remarkably, the nucleophilic addition could be performed highly efficiently and stereoselectively in the presence of diethylzinc in toluene using protected nitrone and alkynyl sugar as reaction partners and thus opens a concise approach to a diversity of disaccharide mimics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.018
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-α-L-arabinofuranoside 在 正丁基锂 、 草酰氯 、 四溴化碳 、 二甲基亚砜 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl 2,3-di-O-benzyl-5,6-dideoxy-β-L-arabino-hex-5-yofuranoside
  参考文献：
  名称：

  Stereoselective synthesis of a novel Galf-disaccharide mimic: β-d-galactofuranosyl-(1-5)-β-d-galactofuranosyl motif of mycobacterial cell walls

  摘要：

  A Galf-disaccharide mimic, an analogue of the acceptor substrates of mycobacterial Galf-transferases, was obtained by nucleophilic addition of a L-arabinofurano-alkyne to iminogalactitol-derived nitrone. Remarkably, the nucleophilic addition could be performed highly efficiently and stereoselectively in the presence of diethylzinc in toluene using protected nitrone and alkynyl sugar as reaction partners and thus opens a concise approach to a diversity of disaccharide mimics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.018