N1-beta-D-吡喃葡萄糖基氨基-胍盐酸盐 | 109853-83-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N1-beta-D-吡喃葡萄糖基氨基-胍盐酸盐
• 英文名称: N''-[(β-D-glucopyranosyl)amino]guanidine nitrate
• 英文别名: nitric acid;2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]guanidine
• CAS: 109853-83-0
• 化学式: C₇H₁₆N₄O₅*HNO₃
• 分子量: 299.241
• InChiKey: FWMFBNDHOWTVBB-WYRLRVFGSA-N

物化性质

• 熔点：
  136-137 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -4.78
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  233
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N1-beta-D-吡喃葡萄糖基氨基-胍盐酸盐 在 sodium acetate 作用下， 反应 0.25h， 以27%的产率得到1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-3-acetamido-5-methyl-1H-1,2,4-triazole
  参考文献：
  名称：

  Cyclization reactions of N1-(glycopyranosylamino) guanidines

  摘要：

  Acetylation of N-1-(aldopyranosylamino)guanidines 2-4 with D-gluco, D-galacto, and L-arabino configuration gives rise to N-1-per(O-acetylglycopyranosylamino)-N-1, N-2, N-3-triacetylguanidines 5-7 in good yields, as already stated by Feather and coworkers [Carbohydr. Res., 267 (1995) 17-25] for the gluco compound. The acylaminoguanidines prepared have been cyclized under mild conditions (boiling in ethanol or treatment with cold 0.1 M sodium methylate solution) to afford 3-amino-N-1-glycopyranosyl-5-methyl-1H-1,2,4-triazoles. The structure of these pyranosyl nucleosides 9, 10, 12-14 is discussed using H-1 and C-13 NMR spectroscopy and mass spectrometry. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00116-x
• 作为产物：
  描述：

  葡萄糖 、 氨基胍硝酸盐 以 水 为溶剂， 以88%的产率得到N1-beta-D-吡喃葡萄糖基氨基-胍盐酸盐
  参考文献：
  名称：

  Novel stereoselective synthesis of 1-(β-d- and α-l-glycopyranosyl)-5-methyl-1H-1,2,4-triazoles

  摘要：

  1-(beta-D- and alpha-L-Glycopyranosyl)-5-methyl-1H-1,2,4-triazoles 7. 13-15 were synthesized stereoselectively from the corresponding glycopyranosyl aminoguanidine nitrates 1-3 in boiling acetic anhydride or from N-1-(acetylated -beta- or or alpha-L-glycopyranosylamino)-N-1,N-2,N-3-triacetylguanidines 8-10 using catalytic amounts of NaOMe. Structures were confirmed by elemental analyses, IR. NMR and MS and possible mechanisms are discussed. In vitro antitumor and immuno activities are presented. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00491-9