α-D-arabinopyranosylamine | 85281-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-arabinopyranosylamine
• 英文别名: (2S,3S,4R,5R)-2-aminooxane-3,4,5-triol
• CAS: 85281-82-9
• 化学式: C₅H₁₁NO₄
• 分子量: 149.147
• InChiKey: RQBSUMJKSOSGJJ-MBMOQRBOSA-N

物化性质

• 熔点：
  124-125 °C
• 沸点：
  340.0±42.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

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：

  氰胺 、 α-D-arabinopyranosylamine 以 甲醇 为溶剂， 反应 48.0h， 以90%的产率得到2-amino-β-D-arabinofurano[1',2':4,5]-oxazoline
  参考文献：
  名称：

  通过糖基胺中间体合成氮15标记的2-氨基（呋喃呋喃）恶唑啉

  摘要：

  摘要提出了一种新的，高效的戊糖和己糖双15N标记的2-氨基-恶唑啉衍生物的合成方法，该方法涉及用氰胺-15N2在甲醇中处理未保护的或O-异丙基亚氨基化的糖基胺，得到2-氨基（呋喃呋喃基）恶唑啉-15N2。提出了这些反应的可能机理。这些技术提供了一种实用的方法，可将各种稳定或放射性同位素引入几种已知的，临床上重要的嘧啶无水核苷中，例如2,2'-脱水-（1-β-d-阿拉伯呋喃糖基胞嘧啶）（环- C）。

  DOI：

  10.1016/0008-6215(83)88113-0
• 作为产物：
  描述：

  α-D-arabinopyranose 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.25h， 生成 α-D-arabinopyranosylamine
  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

• Synthesis of nitrogen-15-labeled 2-amino(glycofurano)oxazolines via glycosylamine intermediates
  作者：Robert M. Davidson、Edward White、Sam A. Margolis、Bruce Coxon

  DOI：10.1016/0008-6215(83)88113-0

  日期：1983.6

  Abstract A new, efficient synthesis of doubly 15N-labeled 2-amino-oxazoline derivatives of pentoses and hexoses has been delineated that involves treatment either of unprotected or O-isopropylidenated glycosylamines with cyanamide-15N2 in methanol to give 2-amino(glycofurano)oxazolines-15N2. A probable mechanism for these reactions is presented. These techniques provide a practical means by which a

  摘要提出了一种新的，高效的戊糖和己糖双15N标记的2-氨基-恶唑啉衍生物的合成方法，该方法涉及用氰胺-15N2在甲醇中处理未保护的或O-异丙基亚氨基化的糖基胺，得到2-氨基（呋喃呋喃基）恶唑啉-15N2。提出了这些反应的可能机理。这些技术提供了一种实用的方法，可将各种稳定或放射性同位素引入几种已知的，临床上重要的嘧啶无水核苷中，例如2,2'-脱水-（1-β-d-阿拉伯呋喃糖基胞嘧啶）（环- C）。
• [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.
• A new, facile synthesis of 2-amino-(pento- and hexo-furano)oxazoline derivatives
  作者：Robert M. Davidson、Sam A. Margolis、Edward White、Bruce Coxon、Norman J. Oppenheimer

  DOI：10.1016/0008-6215(83)88322-0

  日期：1983.1