Azido 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-tridesoxy-6-thio-D-glycero-β-D-galacto-2-nonulopyranosonsaeure-methylester | 109201-80-1

• 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: Azido 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-tridesoxy-6-thio-D-glycero-β-D-galacto-2-nonulopyranosonsaeure-methylester
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-azido-6-[(1R,2R)-1,2,3-triacetyloxypropyl]thiane-2-carboxylate
• CAS: 109201-80-1
• 化学式: C₂₀H₂₈N₄O₁₁S
• 分子量: 532.529
• InChiKey: KXIOOCCQVPHMFD-DCDDNHAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  200
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Azido 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-tridesoxy-6-thio-D-glycero-β-D-galacto-2-nonulopyranosonsaeure-methylester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以61%的产率得到N-acetyl-2-azido-2-desoxy-6-thio-β-neuraminsaeure
  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：

  5-Acetamido-2,4,7,8,9-penta-O-acetyl-3,5-didesoxy-6-thio-D-glycero-β-D-galacto-2-nonulopyranosonsaeure-methylester 在 叠氮基三甲基硅烷 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以88%的产率得到Azido 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-tridesoxy-6-thio-D-glycero-β-D-galacto-2-nonulopyranosonsaeure-methylester
  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