5-Acetamido-3,5-didesoxy-6-thio-D-glycero-D-ido-2-nonulopyranosonsaeure | 109201-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 5-Acetamido-3,5-didesoxy-6-thio-D-glycero-D-ido-2-nonulopyranosonsaeure
• 英文别名: (2S,4R,5S,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]thiane-2-carboxylic acid
• CAS: 109201-71-0
• 化学式: C₁₁H₁₉NO₈S
• 分子量: 325.34
• InChiKey: NVJIKGKSTHUSMD-GLIXCWQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  193
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 5-Acetamido-3,5-didesoxy-6-thio-D-glycero-D-ido-2-nonulopyranosonsaeure 以 甲醇 、 乙醚 为溶剂， 以256 mg的产率得到(2S,4R,5S,6R)-5-Acetylamino-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-thiopyran-2-carboxylic acid methyl ester
  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：

  potassium di-tert-butyloxaloacetate 、 1,4,6-Tri-O-acetyl-2,3-dideoxy-2'-methyl-α-D-mannopyranoso<2,3-d>thiazole 生成 5-Acetamido-3,5-didesoxy-6-thio-D-glycero-D-gulo-2-nonulopyranosonsaeure 、 5-Acetamido-3,5-didesoxy-6-thio-D-glycero-D-ido-2-nonulopyranosonsaeure
  参考文献：
  名称：

  Synthesis of 6-thiosialic acids and 6-thio-N-acetyl-D-neuraminic acid

  摘要：

  DOI：

  10.1016/s0040-4039(00)95683-1

文献信息

• Synthesis of 6-thiosialic acids and 6-thio-N-acetyl-D-neuraminic acid
  作者：H Mack、R Brossmer

  DOI：10.1016/s0040-4039(00)95683-1

  日期：——
• 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.