phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside | 548477-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside
• CAS: 548477-84-5
• 化学式: C₅₃H₄₅N₃O₁₃Se
• 分子量: 1010.91
• InChiKey: XLDWXKSUGKLXSQ-NMTVOFSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  70.0
• 可旋转键数：
  16.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  200.11
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 三甲基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 33.0h， 生成
  参考文献：
  名称：

  A synthetic study towards the PSA1 tetrasaccharide repeating unit

  摘要：

  A synthetic study to the protected tetrasaccharide repeating unit of zwitterionic polysaccharide PSA1 using 1-thio, 1-seleno and 1-hydroxyl functionalized donor glycosides is presented. The ABC trisaccharide part was successfully assembled using an iterative clehydrative glycosylation protocol. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.067
• 作为产物：
  描述：

  2,3,5,6-tetra-O-benzoyl-D-galactofuranose 、 phenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside 在 三氟甲磺酸酐 、 二苯基亚砜 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside
  参考文献：
  名称：

  A synthetic study towards the PSA1 tetrasaccharide repeating unit

  摘要：

  A synthetic study to the protected tetrasaccharide repeating unit of zwitterionic polysaccharide PSA1 using 1-thio, 1-seleno and 1-hydroxyl functionalized donor glycosides is presented. The ABC trisaccharide part was successfully assembled using an iterative clehydrative glycosylation protocol. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.067

文献信息

• Sequential One-Pot Glycosylations Using 1-Hydroxyl and 1-Thiodonors
  作者：Jeroen D. C. Codée、Leendert J. van den Bos、Remy E. J. N. Litjens、Herman S. Overkleeft、Jacques H. van Boom、Gijs A. van der Marel

  DOI：10.1021/ol034528v

  日期：2003.5.1

  [GRAPHIC]A novel sequential glycosylation procedure is described that combines the use of 1-hydroxyl and thiodonors. The Ph2SO/Tf2O-mediated dehydrative condensation of 1-hydroxyl donors with thioglycosides affords in good yield the thiodisaccharides, which in turn can be activated by the same activator system to furnish trisaccharides. The alpha-Gal epitope and a hyaluronan trisaccharide were efficiently assembled in a one-pot procedure.