β-D-mannose thiosemicarbazone | 312738-25-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-mannose thiosemicarbazone
• 英文别名: 2-(β-D-mannopyranosyl)hydrazinecarbothioamide；[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]thiourea
• CAS: 312738-25-3
• 化学式: C₇H₁₅N₃O₅S
• 分子量: 253.279
• InChiKey: YMJWCYLPMHAALV-RWOPYEJCSA-N

物化性质

• 沸点：
  522.6±60.0 °C(predicted)
• 密度：
  1.68±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  16
• 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：
  172
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 β-D-mannose thiosemicarbazone 反应 0.08h， 以88%的产率得到methyl (2E)-2-(4-oxo-2-((β-D-mannopyranosyl)hydrazono)thiazolidin-5-ylidene)acetate
  参考文献：
  名称：

  Facile one-pot synthesis of sugar–thiazolidinone derivatives

  摘要：

  一种简单、高效、经济的方法被描述，用于通过一锅法反应d-半乳糖、d-葡萄糖和d-甘露醇的相应硫脲半羧酸盐，在二甲基或二乙基乙炔二羧酸的存在下合成一系列糖-噻唑烷衍生物。两种不同的方法被使用，并在两种情况下获得高产率：（A）在EtOAC-H2O中，在常温下，（B）在无溶剂条件下进行微波辐射。

  DOI：

  10.1139/v11-123
• 作为产物：
  描述：

  D-甘露糖 、 氨基硫脲 以 乙醇 为溶剂， 生成 β-D-mannose thiosemicarbazone
  参考文献：
  名称：

  Behavior of free sugar thiosemicarbazones toward heterocyclization reactions

  摘要：

  The heterocyclization reaction on thiosemicarbazones having the D-galacto, D-gluco and D-manno configuration was studied. We applied two different acetylating conditions, and the reaction products obtained were identified, spectroscopically characterized, and conformationally analyzed. Using experimental data, we discuss a possible mechanistic pathway for heterocyclization and evaluate the influence of several factors, including starting material configuration, pH of reaction medium, and reaction time.

  DOI：

  10.1016/s0008-6215(00)00127-0

文献信息

• Synthesis of New Gluco-, Galacto-, and Mannopyranosylthiazoles, Thiazolidinones, and Pyranosylthiazlidin-4-ones from Sugar Thiosemicarbazone Derivatives
  作者：Ali Darehkordi、Mahin Ramezani、Reza Ranjbar-Karimi

  DOI：10.1002/hc.21083

  日期：2013.5

  A new series of potentially biological active derivatives, namely alkyl-2-((4-oxo-2-(phenylimino)-3-(β-d-pyranosyl-2-ylamino)thiazolidine-5-ylidene)acetate (5a–f), 4-(4-bromophenyl)thiazol-2(3H)-ylidene)hydrazinyl)-β-d-pyranosyl (4a–c), and 5-(4-bromophenyl)-2-(phenylimino)-3-(β-d-pyranosyl-2-ylamino)thiazolidine-4-one (6) were synthesized via a reaction of the sugar thiosemicarbazone derivatives with

  一系列具有潜在生物活性的新衍生物，即烷基-2-((4-oxo-2-(phenylimino)-3-(β-d-pyranosyl-2-ylamino)thiazolidine-5-ylidene)acetate (5a–f )、4-(4-溴苯基)噻唑-2(3H)-亚基)肼基)-β-d-吡喃糖基(4a-c)和5-(4-溴苯基)-2-(苯基亚氨基)-3-( β-d-吡喃糖基-2-基氨基)噻唑烷-4-酮 (6) 分别通过糖缩氨基硫脲衍生物与 2,4'-二溴苯乙酮、二烷基乙炔二羧酸酯和溴乙酸乙酯的反应合成。通过光谱方法（FT-IR、1H NMR、13C NMR和2D NMR）和元素分析确定合成化合物的结构。此外，回流和环境温度下的各种溶剂对糖缩氨基脲与 2,4'二溴苯乙酮、乙炔二羧酸二乙酯、并研究了乙炔二羧酸二甲酯。© 2013 Wiley Periodicals, Inc. 杂原子化学 24:200–207
• Behavior of free sugar thiosemicarbazones toward heterocyclization reactions
  作者：Miriam A. Martins Alho、Norma B. D'Accorso

  DOI：10.1016/s0008-6215(00)00127-0

  日期：2000.10

  The heterocyclization reaction on thiosemicarbazones having the D-galacto, D-gluco and D-manno configuration was studied. We applied two different acetylating conditions, and the reaction products obtained were identified, spectroscopically characterized, and conformationally analyzed. Using experimental data, we discuss a possible mechanistic pathway for heterocyclization and evaluate the influence of several factors, including starting material configuration, pH of reaction medium, and reaction time.
• Facile one-pot synthesis of sugar–thiazolidinone derivatives
  作者：Ali Darehkordi、Kazem Saidi、Somayeh Ghazi

  DOI：10.1139/v11-123

  日期：2011.11

  A simple, efficient, and cost-effective method for the synthesis of a series of sugar–thiazolidinone derivatives by a one-pot reaction of the corresponding thiosemicarbazone of d-galactose, d-glucose, and d-mannose compounds in the presence of dimethyl or diethyl acetylenedicarboxylate is described. Two different methods were used and high yields were obtained in both cases: (A) in EtOAC–H₂O at an ambient temperature and (B) microwave irradiation under solvent-free conditions.

  一种简单、高效、经济的方法被描述，用于通过一锅法反应d-半乳糖、d-葡萄糖和d-甘露醇的相应硫脲半羧酸盐，在二甲基或二乙基乙炔二羧酸的存在下合成一系列糖-噻唑烷衍生物。两种不同的方法被使用，并在两种情况下获得高产率：（A）在EtOAC-H2O中，在常温下，（B）在无溶剂条件下进行微波辐射。