phenyl 4,6-O-benzylidene-1-seleno-β-D-galactopyranoside | 162060-49-3

• 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: phenyl 4,6-O-benzylidene-1-seleno-β-D-galactopyranoside
• 英文别名: (2S,4aR,6S,7R,8R,8aR)-2-phenyl-6-phenylselanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 162060-49-3
• 化学式: C₁₉H₂₀O₅Se
• 分子量: 407.325
• InChiKey: BESATBIFTAYNCA-VWQYPGANSA-N

物化性质

• 沸点：
  585.6±50.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-benzylidene-1-seleno-β-D-galactopyranoside 在 咪唑 、 sodium hydroxide 、 正丁基锂 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 ((2S,4aR,6S,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-phenylselanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-((2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-ylmethoxy)-dimethyl-silane
  参考文献：
  名称：

  The use of selenophenyl galactopyranosides for the synthesis of α and β-(1→4)-C-disaccharides

  摘要：

  Methyl alpha-C-lactoside (beta-D-Galp-C-(1-->4)-alpha-D-Glcp-OMe) and its alpha anomer were expeditiously synthesized by radical coupling of various selenophenyl galactopyranosides onto methyl 2,3-di-O -benzyl-4-deoxy-4-C-methylene-alpha-D-xylo-hexopyranoside, which are temporarily connected through a silaketal tether.

  DOI：

  10.1016/s0957-4166(00)80403-6
• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-galactopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 phenyl 4,6-O-benzylidene-1-seleno-β-D-galactopyranoside
  参考文献：
  名称：

  The use of selenophenyl galactopyranosides for the synthesis of α and β-(1→4)-C-disaccharides

  摘要：

  Methyl alpha-C-lactoside (beta-D-Galp-C-(1-->4)-alpha-D-Glcp-OMe) and its alpha anomer were expeditiously synthesized by radical coupling of various selenophenyl galactopyranosides onto methyl 2,3-di-O -benzyl-4-deoxy-4-C-methylene-alpha-D-xylo-hexopyranoside, which are temporarily connected through a silaketal tether.

  DOI：

  10.1016/s0957-4166(00)80403-6

文献信息

• Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-β-d-gluco- and galactopyranosides displaying a range of anomeric substituents
  作者：Helen M.I Osborn、Victoria A Brome、Laurence M Harwood、William G Suthers

  DOI：10.1016/s0008-6215(01)00063-5

  日期：2001.5

  The regioselective C-3-O-acylation and O-methylation of a range of 4,6-O-benzylidene-beta -D-gluco- and galactopyranosides has been studied. Regioselectivity is achieved by forming the copper chelate of the 2,3-diol using either sodium hydride and copper(II) chloride, or copper(II) acetylacetanoate, or copper(II) acetate, prior to introduction of the acylating or methylating agent. (C) 2001 Elsevier Science Ltd. All rights reserved.