methyl 2,3-di-O-benzyl-4,6-O-(2-phenylsulfonyl)ethylidene-β-D-galactopyranoside | 280557-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2,3-di-O-benzyl-4,6-O-(2-phenylsulfonyl)ethylidene-β-D-galactopyranoside
• CAS: 280557-36-0
• 化学式: C₂₉H₃₂O₈S
• 分子量: 540.634
• InChiKey: ZAJBIJVVVZTBLB-OROIKLIRSA-N

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-4,6-O-(2-phenylsulfonyl)ethylidene-β-D-galactopyranoside 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以43%的产率得到methyl 2,3-di-O-benzyl-6-O-[(E)-2'-(phenylsulfonyl)vinyl]-α-D-galactopyranoside
  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