β-D-galactopyranosylamine 1,2-(cyclic carbamate) | 100759-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: β-D-galactopyranosylamine 1,2-(cyclic carbamate)
• 英文别名: 1-N,2-O-carbonyl-β-D-galactopyranosylamine；(3aR,5R,6R,7S,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-3,3a,5,6,7,7a-hexahydropyrano[2,3-d][1,3]oxazol-2-one
• CAS: 100759-72-6
• 化学式: C₇H₁₁NO₆
• 分子量: 205.167
• InChiKey: OGXZKGPIPOPCFT-FPRJBGLDSA-N

物化性质

• 熔点：
  187 °C (decomp)
• 沸点：
  638.9±55.0 °C(Predicted)
• 密度：
  1.604±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  诺氟沙星 、 β-D-galactopyranosylamine 1,2-(cyclic carbamate) 以 N,N-二甲基甲酰胺 为溶剂， 以61%的产率得到1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[β-D-galactopyranosylaminocarbonyl]-1-piperazinyl)-3-quinolinecarboxylic acid
  参考文献：
  名称：

  New Carbohydrate Derivatives of Norfloxacin

  摘要：

  New classes of sugar derivatives of the antibacterial drug norfloxacin (1) were synthesized by substituting the N-4' of the piperazinyl moiety of the molecule. Direct coupling with gluco- and galactopyranosyl units afforded glycosylamines 2-5. Introduction of urea or thiourea linkage between glycosyl and norfloxacin units was produced with the corresponding glycosyl isocyanates or isothiocyanates. For the synthesis of unprotected sugar urea compounds, a new approach was applied by using 1,2-N, O-carbonyl-beta-D-glycopyranoses. Hydrazinocarbonyl-methyl- and -propyl spacers also were found appropriate for linking norfloxacin with sugar units.

  DOI：

  10.1081/car-200049410
• 作为产物：
  描述：

  1-叠氮-1-脱氧-β-D-吡喃半乳糖苷 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 β-D-galactopyranosylamine 1,2-(cyclic carbamate)
  参考文献：
  名称：

  Unprotected sugar phosphinimines: A facile route to cyclic carbamates of amino sugars

  摘要：

  DOI：

  10.1016/s0008-6215(00)90755-9

文献信息

• Photo Gel-Sol/Sol-Gel Transition and Its Patterning of a Supramolecular Hydrogel as Stimuli-Responsive Biomaterials
  作者：Shinji Matsumoto、Satoshi Yamaguchi、Shiori Ueno、Harunobu Komatsu、Masato Ikeda、Koji Ishizuka、Yuko Iko、Kazuhito V. Tabata、Hiroyuki Aoki、Shinzaburo Ito、Hiroyuki Noji、Itaru Hamachi

  DOI：10.1002/chem.200701904

  日期：2008.4.28

  photoresponsive supramolecular hydrogelators were discovered, the gel-sol/sol-gel transition of which was pseudo-reversibly induced by light. Studying the optimal hydrogel by NMR spectroscopy and various microscopy techniques showed that the trans-cis photoisomerization of the double bond of the fumaric amide unit effectively caused assembly or disassembly of the self-assembled supramolecular fibers to yield

  在以富马酰胺为反式顺式光开关模块的基于糖脂的水凝剂的聚焦库中，发现了数种新的光响应性超分子水凝剂，其凝胶-溶胶/溶胶-凝胶转变是光可逆地诱导的。通过NMR光谱学和各种显微镜技术研究了最佳水凝胶，结果表明富马酰胺单元双键的反式顺式光异构化有效地导致了自组装超分子纤维的组装或分解，从而分别产生了宏观水凝胶或相应的溶胶。 。超分子纤维的缠结产生了纳米网，根据共聚焦激光扫描显微镜观察，超分子水凝胶中嵌入的纳米珠的尺寸依赖性布朗运动，其空隙空间大致估计为250 nm。清楚地表明，此类纳米网成为捕获亚微米至微米大小底物（如珠子或细菌）的物理障碍。通过利用超分子纳米网的光响应特性，我们成功地关闭/打开了超分子水凝胶中的细菌束缚和串珠拴系的F（1）-ATPase（一种生物分子运动蛋白）的旋转运动。此外，通过使用光刻技术，成功地进行了凝胶-溶胶光图案化以在凝胶基质内产生溶胶点。制成的凝胶-溶胶模式不仅可以在
• Urea Glycoside Synthesis in Water
  作者：Yoshiyasu Ichikawa、Yohei Matsukawa、Minoru Isobe

  DOI：10.1055/s-2004-822902

  日期：——

  A novel approach to the synthesis of urea glycosides in aqueous media has been developed. Reaction of Steyermark’s ­glucosyl carbamate 1 with amines was carried out in water to afford urea glucosides in good yields. This method was successfully ­applied to develop a new route to the synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides.

  我们开发了一种在水介质中合成脲苷的新方法。Steyermark 的氨基甲酸葡糖酯 1 与胺在水中发生反应，以良好的收率得到脲苷。该方法被成功应用于开发一条合成脲系新糖苷和假寡糖的新途径。
• New Carbohydrate Derivatives of Norfloxacin
  作者：Virág Zsoldos‐Mády、Pál Sohár、József Kovács、István Pintér、Zoltán Szakács

  DOI：10.1081/car-200049410

  日期：2005.1

  New classes of sugar derivatives of the antibacterial drug norfloxacin (1) were synthesized by substituting the N-4' of the piperazinyl moiety of the molecule. Direct coupling with gluco- and galactopyranosyl units afforded glycosylamines 2-5. Introduction of urea or thiourea linkage between glycosyl and norfloxacin units was produced with the corresponding glycosyl isocyanates or isothiocyanates. For the synthesis of unprotected sugar urea compounds, a new approach was applied by using 1,2-N, O-carbonyl-beta-D-glycopyranoses. Hydrazinocarbonyl-methyl- and -propyl spacers also were found appropriate for linking norfloxacin with sugar units.
• Unprotected sugar phosphinimines: A facile route to cyclic carbamates of amino sugars
  作者：József Kovács、István Pintér、András Messmer、Gábor Tóth

  DOI：10.1016/s0008-6215(00)90755-9

  日期：1985.8