β-D-ribopyranosylamine | 85280-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-ribopyranosylamine
• 英文别名: D-ribopyranosylamine；D-Ribopyranosylamin；beta-D-Ribopyranosylamine；(2R,3R,4R,5R)-2-aminooxane-3,4,5-triol
• CAS: 85280-61-1
• 化学式: C₅H₁₁NO₄
• 分子量: 149.147
• InChiKey: RQBSUMJKSOSGJJ-TXICZTDVSA-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：

  β-D-ribopyranosylamine 、 trans-1-iodo-2-isocyanatocyclohexane 以 水 、 丙酮 为溶剂， 反应 0.5h， 以81%的产率得到N-(trans-2-iodocyclohexyl)-N'-(β-D-ribopyranosyl)urea
  参考文献：
  名称：

  碳水化合物和糖基氨基-恶唑啉的β-碘尿素衍生物的合成

  摘要：

  摘要N-（β-d-甘露糖基）-N'-（反式-2-碘代环己基）脲（3-7，N-（β-d-吡喃葡萄糖基）-N'-（2-碘-3,3）的合成-二甲基丁基）脲（8和9），N-（2-碘-1,1-二苯乙基）-N'-（β-d-吡喃并吡喃糖基）-脲（10），1,3,4,6-四- O-乙酰基-2-脱氧-2- [3-（反式-2-碘代环己基）脲基]-α-（11）和-β-d-吡喃葡萄糖（12），2-（2,3,4,6， -四-O-乙酰基-β-d-吡喃葡萄糖基氨基）-顺式-3a，4,5,6,7,7a-六氢苯并恶唑（15）和4,4-二苯基-2-（β-d-木吡喃糖基氨基）-报道了2-恶唑啉（16）。

  DOI：

  10.1016/0008-6215(92)84147-k
• 作为产物：
  描述：

  D-核糖 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.25h， 生成 β-D-ribopyranosylamine
  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）。
• First crystallographic evidence for the formation of β-d-ribopyranosylamine from the reaction of ammonia with of d-ribose
  作者：Gudneppanavar Rajsekhar、Chebrolu P Rao、Philippe Guionneau

  DOI：10.1016/s0008-6215(03)00006-5

  日期：2003.4

  Beta-D-Ribopyranosylamine was synthesized and characterized using analytical, spectral and single-crystal X-ray diffraction methods. The molecule exists in the chair form with the 4C(1) conformation. The beta anomeric form of C-1 is supported by the dihedral angles. The molecule exhibits both intra- and intermolecular hydrogen-bond interactions of the type O-H...O, Nz-H...O and C-H...O, and these are

  使用分析，光谱和单晶X射线衍射方法合成并表征了β-D-核吡喃糖基胺。该分子以具有4C（1）构象的椅子形式存在。二面角支持C-1的β端基异构形式。该分子同时表现出OH ... O，Nz-H ... O和CH ... O类型的分子内和分子间氢键相互作用，并且它们相互连接形成链。
• Weng, Min; Jochims, Johannes C., Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 6, p. 530 - 536
  作者：Weng, Min、Jochims, Johannes C.

  DOI：——

  日期：——
• ——
  作者：L. M. Likhosherstov、O. S. Novikova、V. N. Shibaev

  DOI：10.1023/a:1015428720733

  日期：——
• Walczak, Polish Journal of Chemistry, 1999, vol. 73, # 5, p. 799 - 804
  作者：Walczak

  DOI：——

  日期：——