2-benzylamino-2-deoxy-3-O-(β-D-galactopyranosyl)-D-arabinose | 209671-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzylamino-2-deoxy-3-O-(β-D-galactopyranosyl)-D-arabinose
• 英文别名: 1-N-benzyl-3-O-β-D-galactopyranosyl-D-arabinosylamine；(2S,3R,4S,5R,6R)-2-[(2R,3S,4S)-5-(benzylamino)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 209671-44-3
• 化学式: C₁₈H₂₇NO₉
• 分子量: 401.414
• InChiKey: VPEXEQUENVYJSY-YTDZRJAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  161
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-benzylamino-2-deoxy-3-O-(β-D-galactopyranosyl)-D-arabinose 在 palladium on barium sulfate 氢气 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 42.0h， 生成 N-acetyl-D-lactosamine
  参考文献：
  名称：

  A convenient synthesis of N-acetyllactosamine

  摘要：

  DOI：

  10.1016/s0008-6215(00)80763-6
• 作为产物：
  描述：

  3-O-(β-D-galactopyranosyl)-D-arabinose 、 苄胺 以 乙醇 为溶剂， 反应 1.5h， 以91.0 g的产率得到2-benzylamino-2-deoxy-3-O-(β-D-galactopyranosyl)-D-arabinose
  参考文献：
  名称：

  Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine

  摘要：

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00294-4

文献信息

• A convenient synthesis of N-acetyllactosamine
  作者：Jocelyne Alais、Alain Veyrières

  DOI：10.1016/s0008-6215(00)80763-6

  日期：1981.6
• Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine
  作者：Gerhard Kretzschmar、Wilhelm Stahl

  DOI：10.1016/s0040-4020(98)00294-4

  日期：1998.6

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.