methyl 2,3-di-O-benzyl-6-O-[(E)-2'-(phenylsulfonyl)pent-1'-enyl]-α-D-glucopyranoside | 1353644-84-4

• 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-6-O-[(E)-2'-(phenylsulfonyl)pent-1'-enyl]-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-[[(E)-2-(benzenesulfonyl)pent-1-enoxy]methyl]-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 1353644-84-4
• 化学式: C₃₂H₃₈O₈S
• 分子量: 582.715
• InChiKey: KMFYSLZQULIJAS-TZXFXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-碘代丙烷 、 methyl 2,3-di-O-benzyl-4,6-O-(2-phenylsulphonyl)-ethylidene-α-D-glucopyranoside 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以32%的产率得到methyl 2,3-di-O-benzyl-6-O-[(E)-2'-(phenylsulfonyl)pent-1'-enyl]-α-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrate-derived PSE acetals: controlled base-induced ring cleavage

  摘要：

  Retro-Michael type reactions applied to PSE acetals protecting monosaccharides led either to complete removal or to ring-cleavage. In protic medium, application of standard basic conditions resulted in acetal deprotection, while the use of butyl lithium in aprotic medium allowed controlled ring-cleavage. A regio-and stereoselective C- over O-alkylation was observed during the process. Furthermore, depending on the substrates and the reaction conditions involved, new carbohydrate-derived beta-alkoxyvinyl sulfones were obtained with varying regioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.009

文献信息

• Carbohydrate-derived PSE acetals: controlled base-induced ring cleavage
  作者：Florence Chéry、Elena Cabianca、Arnaud Tatibouët、Ottorino De Lucchi、Patrick Rollin

  DOI：10.1016/j.tet.2011.11.009

  日期：2012.1

  Retro-Michael type reactions applied to PSE acetals protecting monosaccharides led either to complete removal or to ring-cleavage. In protic medium, application of standard basic conditions resulted in acetal deprotection, while the use of butyl lithium in aprotic medium allowed controlled ring-cleavage. A regio-and stereoselective C- over O-alkylation was observed during the process. Furthermore, depending on the substrates and the reaction conditions involved, new carbohydrate-derived beta-alkoxyvinyl sulfones were obtained with varying regioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.