N-(o-tolyl)-β-D-mannopyranosylamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(o-tolyl)-β-D-mannopyranosylamine
• 英文别名: (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-(2-methylanilino)oxane-3,4,5-triol
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: DVSPJWLNHJGHJA-NAWOPXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-甘露糖 、 邻甲苯胺 以 水 为溶剂， 以92.8%的产率得到N-(o-tolyl)-β-D-mannopyranosylamine
  参考文献：
  名称：

  N-tolyglycosylamines 的合成和表征

  摘要：

  N-甲苯基糖胺由邻-、间-和对-甲苯胺和醛糖（D-葡萄糖、D-半乳糖、D-甘露糖、L-鼠李糖、D-木糖和L-阿拉伯糖）合成。使用 13 C NMR 方法确定合成产物的异头和异构组成。

  DOI：

  10.1007/s10600-008-9095-y

文献信息

• Molecular and crystal structures of N-aryl-β-d-glycopyranosylamines from mannose and galactose
  作者：Charles R Ojala、Joanne M Ostman、Summer E Hanson、William H Ojala

  DOI：10.1016/s0008-6215(01)00117-3

  日期：2001.6

  The molecular and crystal structures of 12 N-aryl-beta -D-glycopyranosylamines have been determined by X-ray crystallography. Six of these are mannose derivatives, the N-p-bromophenyl (1), N-p-tolyl (2), N-m-chlorophenyl (3), N-p-methoxyphenyl (4), N-o-chloroyhenyl (5), and N-o-tolyl (6) derivatives that are formed by reaction with the corresponding substituted anilines. The remaining six are galactose derivatives, the N-phenyl (7), N-p-chlorophenyl (8), N-p-bromophenyl (9), N-p-iodophenyl (10), N-p-nitrophenyl (11) and N-p-tolyl (12), derivatives prepared similarly. Compounds 1 3 assume the same packing arrangement. Compounds 4, 5, and 6 assume unique packing an arrangements, although that assumed by 4 is closely related to that assumed by 1-3. Compounds 7-11 assume the same packing arrangement; that assumed by 12 is closely related to that assumed by 7-11. That the same packing arrangements can be maintained in spite of substantial changes in the electronic and steric nature of the substituent on the aryl ring reflects the strength of the hydrogen bond network connecting the monosaccharide portions of the molecules in the solid state. A hydrogen bonding motif found in all six mannose structures is a mutual interaction between translationally related molecules involving 0-3-(HO)-O-...-5 and O-6-(HO)-O-...-4 hydrogen bonds. The recurrence of this motif throughout this group of mannosylamines suggests that it is an especially favorable interaction that might be expected to occur also in related macromolecular systems. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis and characterization of N-tolyglycosylamines
  作者：R. I. Kublashvili、M. O. Labartkava、K. P. Giorgadze、D. Sh. Ugrekhelidze

  DOI：10.1007/s10600-008-9095-y

  日期：2008.7

  N-Tolylglycosylamines were synthesized from o-, m-, and p-toluidines and aldoses (D-glucose, D-galactose, D-mannose, L-rhamnose, D-xylose, and L-arabinose). The anomeric and isomeric compositions of the synthesized products were established using 13C NMR methods.

  N-甲苯基糖胺由邻-、间-和对-甲苯胺和醛糖（D-葡萄糖、D-半乳糖、D-甘露糖、L-鼠李糖、D-木糖和L-阿拉伯糖）合成。使用 13 C NMR 方法确定合成产物的异头和异构组成。