2-O-acetyl-3,4,5,7-tetra-O-benzyl-α-D-galactono-1,5-lactone | 145150-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-acetyl-3,4,5,7-tetra-O-benzyl-α-D-galactono-1,5-lactone
• 英文别名: [(3R,4S,5S,6R)-2-oxo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 145150-08-9
• 化学式: C₂₉H₃₀O₇
• 分子量: 490.553
• InChiKey: QCOWRTWDWZUUBD-WXIAYYLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,5,7-tetra-O-benzyl-α-D-galactono-1,5-lactone 在 potassium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 生成 (3R,4R,5S,6R)-2-methylidene-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
  参考文献：
  名称：

  Selective radical synthesis of β- C -disaccharides

  摘要：

  Several P-C-disaccharides have been selectively synthesized by radical cyclization of two temporarily tethered functionalized monosaccharides. In this process, intramolecular addition of a carbohydrate-derived radical onto an anomeric exomethylene group, followed by axial hydrogen addition, resulted in beta stereochemistry. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01533-7
• 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 吡啶 、 溶剂黄146 、 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 水 、 二氯甲烷 为溶剂， 生成 2-O-acetyl-3,4,5,7-tetra-O-benzyl-α-D-galactono-1,5-lactone
  参考文献：
  名称：

  Selective radical synthesis of β- C -disaccharides

  摘要：

  Several P-C-disaccharides have been selectively synthesized by radical cyclization of two temporarily tethered functionalized monosaccharides. In this process, intramolecular addition of a carbohydrate-derived radical onto an anomeric exomethylene group, followed by axial hydrogen addition, resulted in beta stereochemistry. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01533-7

文献信息

• Synthesis and glycosylating properties of ketopyranosyl donors
  作者：B.M. Heskamp、G.H. Veeneman、G.A. van der Marel、C.A.A. van Boeckel、J.H. van Boom

  DOI：10.1016/0040-4020(95)00225-w

  日期：1995.5

  The preparation of heptulopyranosyl donors 13-15, 28, 29 and 3-octulopyranosyl donors 34, 35, having a non-participating group at C-3 or C-4, respectively, is described. Glycosylations of various accepters with these donors gave exclusively cc-linked ketosides. On the other hand, condensation of 3-O-benzoyl heptulopyranosyl donor 19 with art acceptor furnished an anomeric mixture of ketodisaccharides.