2-Acetamido-2-desoxy-5,6-O-isopropyliden-3-thio-D-mannofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Acetamido-2-desoxy-5,6-O-isopropyliden-3-thio-D-mannofuranose
• 英文别名: 2-Acetamido-2-deoxy-5,6-O-isopropylidene-3-thio-α,β-D-mannofurannose；N-[(3R,4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxy-4-sulfanyloxolan-3-yl]acetamide
• 化学式: C₁₁H₁₉NO₅S
• 分子量: 277.342
• InChiKey: FZHSCZNILDMXJV-QWIPYHCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  78
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  草酰乙酸 、 2-Acetamido-2-desoxy-5,6-O-isopropyliden-3-thio-D-mannofuranose 在 sodium hydroxide 、 nickel diacetate 作用下， 以 水 为溶剂， 以64%的产率得到
  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-α-D-mannopyrano-<2',3':4,5>-2-thiazoline 在 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 2-Acetamido-2-desoxy-5,6-O-isopropyliden-3-thio-D-mannofuranose
  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

• 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.