(2S,3S,4R,5R)-2-(15N)azanyloxane-3,4,5-triol | 1053247-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R)-2-(15N)azanyloxane-3,4,5-triol
• CAS: 1053247-05-4
• 化学式: C₅H₁₁NO₄
• 分子量: 150.14
• InChiKey: RQBSUMJKSOSGJJ-BDZYNMLLSA-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：

  (2S,3S,4R,5R)-2-(15N)azanyloxane-3,4,5-triol 、 POTASSIUM CYANIDE-13C 在 Pd-BaSO₄ 溶剂黄146 、 氢气 、 Dowex resin H⁽¹⁺⁾ form 作用下， 以 水 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 0.1h， 生成 、 Glucosamine-13C,15N (hydrochloride)
  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
• 作为产物：
  描述：

  α-D-arabinopyranose 在 15N-氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (2S,3S,4R,5R)-2-(15N)azanyloxane-3,4,5-triol
  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

文献信息

• [¹³C,¹⁵N]2-Acetamido-2-deoxy-<scp>d</scp>-aldohexoses and Their Methyl Glycosides:  Synthesis and NMR Investigations of <i>J</i>-Couplings Involving ¹H, ¹³C, and ¹⁵N
  作者：Yuping Zhu、Qingfeng Pan、Christophe Thibaudeau、Shikai Zhao、Ian Carmichael、Anthony S. Serianni

  DOI：10.1021/jo051510k

  日期：2006.1.1

  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.