Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[N-acetyl-N'-(bis-acetylamino-methylene)-hydrazino]-tetrahydro-pyran-3-yl ester | 162191-11-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[N-acetyl-N'-(bis-acetylamino-methylene)-hydrazino]-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3R,4S,5R,6R)-6-[acetyl-(diacetamidomethylideneamino)amino]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 162191-11-9
• 化学式: C₂₁H₃₀N₄O₁₂
• 分子量: 530.489
• InChiKey: ITLLBAGCXMGMPB-OUUBHVDSSA-N

物化性质

• 熔点：
  171-172 °C
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  205
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[N-acetyl-N'-(bis-acetylamino-methylene)-hydrazino]-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 32.0h， 以72%的产率得到(2R,3R,4S,5S,6R)-2-(3-Amino-5-methyl-[1,2,4]triazol-1-yl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  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：

  乙酸酐 、 β-D-glucopyranosyl aminoguanidine trifluoroacetate salt 在 吡啶 作用下， 反应 24.0h， 以42.7%的产率得到Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[N-acetyl-N'-(bis-acetylamino-methylene)-hydrazino]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  D-葡萄糖与氨基胍的反应。

  摘要：

  在pH 7.0和37摄氏度（磷酸盐缓冲液）下检查了D-葡萄糖与氨基胍的反应。在这些条件下，该反应需要约。42天后50％的糖发生反应（通过D-葡萄糖的消失来衡量），并且所有氨基胍在60摄氏度下在72小时内反应了。以结晶状态获得作为三氟乙酸盐的初始产物β-D-吡喃葡萄糖基氨基胍（1）。关于该化合物的数据表明，在溶液中，它主要是β-吡喃糖形式的糖胺。乙酰化得到结晶的七乙酸盐（2），其在溶液中（由NMR光谱证实）以两种不同的构象形式存在。七乙酸酯的晶体结构还包括两个构象体。

  DOI：

  10.1016/0008-6215(94)00285-n

文献信息

• Novel stereoselective synthesis of 1-(β-d- and α-l-glycopyranosyl)-5-methyl-1H-1,2,4-triazoles
  作者：Jianxin Yu、Zhongjun Li、Wenjie Lu、Suna Zhang、Mengshen Cai

  DOI：10.1016/s0957-4166(03)00491-9

  日期：2003.9

  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.