2-Methyl-4,5-dihydro-(2,3-didesoxy-α-D-mannofuranoso)[2,3-d]-1,3-thiazol | 207506-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-Methyl-4,5-dihydro-(2,3-didesoxy-α-D-mannofuranoso)[2,3-d]-1,3-thiazol
• 英文别名: (1R)-1-[(3aR,4S,6R,6aR)-4-hydroxy-2-methyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]thiazol-6-yl]ethane-1,2-diol
• CAS: 207506-31-8
• 化学式: C₈H₁₃NO₄S
• 分子量: 219.262
• InChiKey: CZQOVMXBYOXBJJ-UOLFYFMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Methyl-4,5-dihydro-(2,3-didesoxy-α-D-mannofuranoso)[2,3-d]-1,3-thiazol 在 吡啶 、 盐酸 作用下， 反应 92.0h， 生成 2-Acetamido-1,4,6-tri-O-acetyl-3-S-acetyl-2-desoxy-3-thio-β-D-mannopyranose
  参考文献：
  名称：

  Synthese von 6-thiosialinsäuren

  摘要：

  The synthesis of 2-acetamido-2-deoxy-3-thio-D-mannose (11) is described. Chain elongation of thiazoline 10 with potassium-di-O-tbutyl-oxaloacetate yields epimeric 6-thiosialic acids 14 and 15. Chain extension of 18 with oxaloacetate/Ni++ results in the formation of N-acetyl-6-thioneuraminic acid (21). Starting from 21 synthesis of alpha-azide 25 and dehydro-compound 27 was accomplished by treatment of 23 with sodium azide. On the other hand lewis acid catalyzed azidation of 22 beta with azidotrimethylsilane afforded beta-azide 29. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00167-7
• 作为产物：
  描述：

  2-Methyl-4,5-dihydro-(1,4,6-tri-O-acetyl-2,3-didesoxy-β-D-mannopyranoso)[2,3-d]-1,3-thiazol 在 二乙胺 作用下， 以 甲醇 为溶剂， 反应 60.0h， 以78%的产率得到2-Methyl-4,5-dihydro-(2,3-didesoxy-α-D-mannofuranoso)[2,3-d]-1,3-thiazol
  参考文献：
  名称：

  Synthese von 6-thiosialinsäuren

  摘要：

  The synthesis of 2-acetamido-2-deoxy-3-thio-D-mannose (11) is described. Chain elongation of thiazoline 10 with potassium-di-O-tbutyl-oxaloacetate yields epimeric 6-thiosialic acids 14 and 15. Chain extension of 18 with oxaloacetate/Ni++ results in the formation of N-acetyl-6-thioneuraminic acid (21). Starting from 21 synthesis of alpha-azide 25 and dehydro-compound 27 was accomplished by treatment of 23 with sodium azide. On the other hand lewis acid catalyzed azidation of 22 beta with azidotrimethylsilane afforded beta-azide 29. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00167-7

文献信息

• Synthese von 6-thiosialinsäuren
  作者：Hans Mack、Reinhard Brossmer

  DOI：10.1016/s0040-4020(98)00167-7

  日期：1998.4

  The synthesis of 2-acetamido-2-deoxy-3-thio-D-mannose (11) is described. Chain elongation of thiazoline 10 with potassium-di-O-tbutyl-oxaloacetate yields epimeric 6-thiosialic acids 14 and 15. Chain extension of 18 with oxaloacetate/Ni++ results in the formation of N-acetyl-6-thioneuraminic acid (21). Starting from 21 synthesis of alpha-azide 25 and dehydro-compound 27 was accomplished by treatment of 23 with sodium azide. On the other hand lewis acid catalyzed azidation of 22 beta with azidotrimethylsilane afforded beta-azide 29. (C) 1998 Elsevier Science Ltd. All rights reserved.