(2S,3R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]thiane-2,3-dicarboxylic acid | 109201-75-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]thiane-2,3-dicarboxylic acid
• CAS: 109201-75-4
• 化学式: C₁₂H₁₉NO₁₀S
• 分子量: 369.35
• InChiKey: QOFCMVNWVUSQSN-JSDHTTBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  230
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]thiane-2,3-dicarboxylic acid 在 氢气 作用下， 以 吡啶 、 水 为溶剂， 生成 Azido 5-acetamido-2,3,5-tridesoxy-6-thio-D-glycero-α-D-galacto-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
• 作为产物：
  描述：

  在 Amberlite IR 120 、 氢气 作用下， 以 水 为溶剂， 反应 3.0h， 以20 mg的产率得到(2S,3R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]thiane-2,3-dicarboxylic acid
  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

• Kok, Gaik B.; Campbell, Michael; Mackey, Brendan, Journal of the Chemical Society. Perkin transactions I, 1996, # 23, p. 2811 - 2815
  作者：Kok, Gaik B.、Campbell, Michael、Mackey, Brendan、Von Itzstein, Mark

  DOI：——

  日期：——
• 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.