2-O-acetyl-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone | 384819-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone
• 英文别名: [(3R,4S,5R,6R)-2-oxo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 384819-72-1
• 化学式: C₂₉H₃₀O₇
• 分子量: 490.553
• InChiKey: QCOWRTWDWZUUBD-ZZXHUEHTSA-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-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 在 potassium osmate(VI) dihydrate 、 potassium hexacyanoferrate(III) 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 71.0h， 生成 4,5,7-tri-O-benzyl-α-D-glucohept-2-ulopyranose
  参考文献：
  名称：

  Expedient and Versatile Formation of Novel Amino-deoxy-ketoheptuloses

  摘要：

  Novel monoketoheptuloses have been synthesized employing an amination step in a pre- and/or post-C1 chain elongation using a Petasis reagent by starting from aldohexoses or aldohexosamines. A series of gluco and manno configured 1-/3-deoxy-1-/3-amino-ketohept-2-uloses could be obtained.

  DOI：

  10.1021/ol4021699
• 作为产物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 在 乙酸酐 、 二甲基亚砜 作用下， 以79%的产率得到2-O-acetyl-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone
  参考文献：
  名称：

  Expedient and Versatile Formation of Novel Amino-deoxy-ketoheptuloses

  摘要：

  Novel monoketoheptuloses have been synthesized employing an amination step in a pre- and/or post-C1 chain elongation using a Petasis reagent by starting from aldohexoses or aldohexosamines. A series of gluco and manno configured 1-/3-deoxy-1-/3-amino-ketohept-2-uloses could be obtained.

  DOI：

  10.1021/ol4021699

文献信息

• Selective radical synthesis of β- C -disaccharides
  作者：Boris Vauzeilles、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(01)01533-7

  日期：2001.10

  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.