5-Acetamido-2,4,7,8,9-penta-O-acetyl-3,5-didesoxy-6-thio-D-glycero-β-D-galacto-2-nonulopyranosonsaeure-methylester | 109201-77-6

• 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: 5-Acetamido-2,4,7,8,9-penta-O-acetyl-3,5-didesoxy-6-thio-D-glycero-β-D-galacto-2-nonulopyranosonsaeure-methylester
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1R,2R)-1,2,3-triacetyloxypropyl]thiane-2-carboxylate
• CAS: 109201-77-6
• 化学式: C₂₂H₃₁NO₁₃S
• 分子量: 549.553
• InChiKey: LUUIDWQYACKRHV-QDRUEPRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  212
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  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 盐酸 、 sodium azide 作用下， 以 乙酸酐 、 溶剂黄146 、 丙酮 为溶剂， 反应 48.0h， 生成 5-Acetamido-2,6-anhydro-3,5-didesoxy-6-thio-D-glycero-D-galacto-non-2-ensaeure
  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：

  重氮甲烷 、 (2S,4S,5R,6R)-2,4-Diacetoxy-5-acetylamino-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-thiopyran-2-carboxylic acid 以 甲醇 、 乙醚 为溶剂， 以807 mg的产率得到5-Acetamido-2,4,7,8,9-penta-O-acetyl-3,5-didesoxy-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