phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-galactopyranoside | 162060-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-galactopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylselanyloxan-3-ol
• CAS: 162060-48-2
• 化学式: C₃₃H₃₄O₅Se
• 分子量: 589.59
• InChiKey: VCDIZJLUSYCNEO-AALIFHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-galactopyranoside 在 吡啶 、 咪唑 、 正丁基锂 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 17.0h， 生成 Acetic acid (2S,3R,4S,5R,6R)-3-((2S,3S,4S,5S,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-5-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  A stereoselective synthesis of methyl β-C-lactoside through the tether approach

  摘要：

  Methyl beta-C-lactoside (beta-D-Galp-C-(1-->4)-beta-Glcp-OMe) is stereoselectively synthesized by radical coupling of phenyl Se-beta-D-galactopyranoside 5 onto exo-methylene-sugar 4, which are temporarily connected through a silaketal tether. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00649-2
• 作为产物：
  描述：

  2,3,5-三邻苄基-1-o-(4-硝基苯甲酰基)-d-阿拉伯呋喃糖 在 sodium methylate 、 mercury dibromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 phenyl 3,4,6-tri-O-benzyl-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

• Stereoselective Synthesis of β-Phenylselenoglycosides from Glycals and Rationalization of the Selenoglycosylation Processes
  作者：Valeria Di Bussolo、Annalisa Fiasella、Federica Balzano、Gloria Uccello Barretta、Paolo Crotti

  DOI：10.1021/jo100145s

  日期：2010.6.18

  beta-Phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe(-)) with glycals. A rationalization of the presently described beta-selectivity and the opposite alpha-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.
• DE, MESMAEKER ALAIN;HOFFMANN, PASCALE;ERNST, BEAT;HUG, PAUL;WINKLER, TAMM+, TETRAHEDRON LETT., 30,(1989) N6, C. 6311-6314
  作者：DE, MESMAEKER ALAIN、HOFFMANN, PASCALE、ERNST, BEAT、HUG, PAUL、WINKLER, TAMM+

  DOI：——

  日期：——
• The use of selenophenyl galactopyranosides for the synthesis of α and β-(1→4)-C-disaccharides
  作者：Astrid Mallet、Jean-Maurice Mallet、Pierre Sinay

  DOI：10.1016/s0957-4166(00)80403-6

  日期：1994.12

  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.
• A stereoselective synthesis of methyl β-C-lactoside through the tether approach
  作者：Gilles Rubinstenn、Jean-Maurice Mallet、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(98)00649-2

  日期：1998.5

  Methyl beta-C-lactoside (beta-D-Galp-C-(1-->4)-beta-Glcp-OMe) is stereoselectively synthesized by radical coupling of phenyl Se-beta-D-galactopyranoside 5 onto exo-methylene-sugar 4, which are temporarily connected through a silaketal tether. (C) 1998 Elsevier Science Ltd. All rights reserved.