5-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose | 1010809-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose
• 英文别名: tert-butyl N-[2-[[(1S)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl]carbamothioylamino]ethyl]carbamate
• CAS: 1010809-42-3
• 化学式: C₁₇H₃₁N₃O₇S
• 分子量: 421.515
• InChiKey: QWQWGEYXVLECLU-KIJLLGNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose 、 乙酸酐 在 吡啶 作用下， 反应 2.0h， 以90%的产率得到3,6-di-O-acetyl-5-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Guanidine-Type Iminosugars

  摘要：

  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose -> piperidine rearrangement of 5-deoxy-5guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.

  DOI：

  10.1021/jo702374f
• 作为产物：
  描述：

  5-amino-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose 、 N-Boc-2-异硫氰酰基乙胺 在 吡啶 作用下， 反应 16.0h， 以82%的产率得到5-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Guanidine-Type Iminosugars

  摘要：

  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose -> piperidine rearrangement of 5-deoxy-5guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.

  DOI：

  10.1021/jo702374f

文献信息

• Synthesis and Biological Evaluation of Guanidine-Type Iminosugars
  作者：Matilde Aguilar、Paula Díaz-Pérez、M. Isabel García-Moreno、Carmen Ortiz Mellet,* and、José M. García Fernández

  DOI：10.1021/jo702374f

  日期：2008.3.1

  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose -> piperidine rearrangement of 5-deoxy-5guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.