2-Methyl-4,5-dihydro-(2,3-didesoxy-5,6-O-isopropyliden-α-D-mannofuranoso)[2,3-d]-1,3-thiazol | 109201-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methyl-4,5-dihydro-(2,3-didesoxy-5,6-O-isopropyliden-α-D-mannofuranoso)[2,3-d]-1,3-thiazol
• 英文别名: (3aR,4S,6R,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]thiazol-4-ol
• CAS: 109201-82-3
• 化学式: C₁₁H₁₇NO₄S
• 分子量: 259.326
• InChiKey: JXVZBKOUQDBIGI-ZOZBQHSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Methyl-4,5-dihydro-(2,3-didesoxy-5,6-O-isopropyliden-α-D-mannofuranoso)[2,3-d]-1,3-thiazol 在 吡啶 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 96.0h， 生成 2-Acetamido-1-O-acetyl-3-S-acetyl-5,6-O-isopropyliden-2-desoxy-3-thio-β-D-mannofuranose
  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 硫酸 、 二乙胺 作用下， 以 甲醇 为溶剂， 反应 60.0h， 生成 2-Methyl-4,5-dihydro-(2,3-didesoxy-5,6-O-isopropyliden-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

• 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.