beta-D-来苏吡喃糖基胺 | 501947-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: beta-D-来苏吡喃糖基胺
• 英文名称: β-D-lyxopyranosylamine
• 英文别名: (2R,3S,4S,5R)-2-Aminotetrahydro-2H-pyran-3,4,5-triol；(2R,3S,4S,5R)-2-aminooxane-3,4,5-triol
• CAS: 501947-89-3
• 化学式: C₅H₁₁NO₄
• 分子量: 149.147
• InChiKey: RQBSUMJKSOSGJJ-MGCNEYSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  95.9
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  beta-D-来苏吡喃糖基胺 、 3,4-二甲氧基-3-环丁烯-1,2-二酮 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以48%的产率得到3-methoxy-4-[[(2R,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]amino]cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Application of Squaric Acid Esters in Aminodeoxy Sugar Chemistry

  摘要：

  二甲基方酸酯与氨基去氧糖、氨基去氧醇、氨基醛酸和糖基胺在中性条件下反应，生成了方酸酰胺酯，这些方酸酰胺酯在更碱性的介质（pH≈8）中转化成不对称方酸二酰胺。不受保护的方酸酰胺酯适合用于构建特定的锚固（间隔、连接）功能，这些功能对生成的药物和糖缀合物的水溶性有积极影响。

  DOI：

  10.1246/cl.2007.1012
• 作为产物：
  描述：

  D-来苏糖 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.25h， 生成 beta-D-来苏吡喃糖基胺
  参考文献：
  名称：

  [¹³C,¹⁵N]2-Acetamido-2-deoxy-d-aldohexoses and Their Methyl Glycosides:  Synthesis and NMR Investigations of J-Couplings Involving ¹H, ¹³C, and ¹⁵N

  摘要：

  A series of 2-amino-2-deoxy-D-[1-C-13]aldohexoses and their methyl glycosides was prepared with use of a simplified cyanohydrin reduction route. Four D-aldopentosylamines (arabino, lyxo, ribo, xylo) were prepared from the corresponding D-aldopentoses by reaction with NH3(9) in MeOH solvent, isolated in solid form, and characterized by C-13 and H-1 NMR. Hydrolysis of beta-D-xylopyranosylamine was studied using C-13-labeled substrates to establish optimal solution conditions for cyanohydrin formation. Major hydrolytic intermediates were observed and identified by time-lapse 1D and 2D NMR analyses of reaction mixtures. The aldopentosylamines were subsequently employed in cyanohydrin reduction reactions with (KCN)-C-13 to yield C2-epimeric [1-C-13]2-aminosugars, which were separated by chromatography on ion-exchange columns. N-Acetylation and methyl glycosidation followed by chromatography gave pure 2-acet-amido-2-deoxy-D-[ 1-C-13]aldobexopyranosides. J(CH) and J(CC) spin-spin coupling constants involving the labeled anomeric carbon were measured and compared to those observed previously in methyl D-[1-C-13]-aldohexopyrano sides. In parallel studies, theoretical J-couplings were calculated in model N-acetylated aldopyranosides using density functional theory (DFT) to predict the effect of OH vs NHCOCH3 substitution at C2 on J(CH) and J(CC) values in aldopyranosyl rings. The synthetic method was also modified to accommodate N-15- and C-13-labeling within the N-acetyl side-chain, and some J-couplings involving 1H, C-13, and N-15 atoms in 2-[1,2-C-13(2);N-15]acetamido-2-deoxy-D-[1-C-13]glucose were measured and interpreted.

  DOI：

  10.1021/jo051510k