N-(4-nitrophenyl)-D-galactosylamine | 10399-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-nitrophenyl)-D-galactosylamine
• 英文别名: (2R,3R,4S,5R)-2-(hydroxymethyl)-6-(4-nitroanilino)oxane-3,4,5-triol
• CAS: 10399-84-5
• 化学式: C₁₂H₁₆N₂O₇
• 分子量: 300.268
• InChiKey: ONVNCZJMOXIVHT-SCWFEDMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  148
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenyl)-D-galactosylamine 、 碘甲烷 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以82%的产率得到N-methyl-N-(4-nitrophenyl)-2,3,4,6-tetra-O-methyl-β-D-galactopyranosylamine
  参考文献：
  名称：

  Selective defucosylation by mercaptolysis. A potential step in analyzing branched oligosaccharides

  摘要：

  A method of stepwise chemical degradation was elaborated on a mu g quantity of 3-O-alpha-L-fucosyllactose. The key step, TiCl4-catalysed dithioacetal formation from the permethylated N-4-nitrophenyl triosylamine (4) was accompanied by quantitative defucosylation. [C-14]Acetylation of the dried mercaptalation mixture gave radiolabelled 3,5-di-O-[C-14]acetyl-4-O-(2,3,4,6-tetra-O-methyl-beta-D-galactopyranosyl)-2,6-diO-methyl-D-glucose diethyl dithioacetal (7) and 5-O-[C-14]acetyl-2,3,4-tri-O-methyl-L-fucose diethyl dithioacetal (8). The former was further degraded via the bis(sulfone), and thereby 2,3,4,6-tetra-O-methyl-D-galactose (13) was expelled. The monosaccharide branches, fucose and galactose, were identified as derivatives 8 and 13, respectively, by comparison with authentic samples. Isolation of microquantities of products was carried out by preparative TLC.

  DOI：

  10.1016/s0008-6215(05)80006-0