2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-D-galactono-1,4-lactone | 849414-56-8

• 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: 2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-D-galactono-1,4-lactone
• CAS: 849414-56-8
• 化学式: C₁₄H₁₈O₉S
• 分子量: 362.358
• InChiKey: LKGHVDVNPFQVHD-MROQNXINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.01
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  122.27
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-D-galactono-1,4-lactone 在 二(3-甲基丁烷-2-基)硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-α-D-galactofuranose 、 2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-β-D-galactofuranose
  参考文献：
  名称：

  First synthesis of 4,5-O-isopropylidene-6-thio-d-galactono-1,6-lactone as a precursor of d-galactothioseptanose

  摘要：

  Displacement of the bromide group in methyl 6-bromo-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate 7, with potassium thioacetate gave methyl 6-(S)-acetyl-2,3 :4,5-di-O-isopropylidene-6-thio-D-galactonate 8 in quantitative yield. Regioselective removal of the 2,3-ketal protecting group afforded methyl 6-(S)-acetyl-4,5-O-isopropylidene-6-thio-D-galactonate 11 in 70% yield. Saponification of compound 11 gave the 6-(S)-4,5-O-isopropylidene-6-thio-D-galactonic acid 12 in quantitative yield. Treatment of 12 with DIC/HOBt as coupling reagents gave, after cyclisation; the target compound: 4,5-O-isopropylidene 6-thio-D-galactono-1,6-lactone 13 in 49% yield. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.088
• 作为产物：
  描述：

  6-bromo-6-deoxy-D-galactono-1,4-lactone 在 高氯酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 2,3,5-tri-O-acetyl-6-S-acetyl-6-thio-D-galactono-1,4-lactone
  参考文献：
  名称：

  First synthesis of 4,5-O-isopropylidene-6-thio-d-galactono-1,6-lactone as a precursor of d-galactothioseptanose

  摘要：

  Displacement of the bromide group in methyl 6-bromo-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate 7, with potassium thioacetate gave methyl 6-(S)-acetyl-2,3 :4,5-di-O-isopropylidene-6-thio-D-galactonate 8 in quantitative yield. Regioselective removal of the 2,3-ketal protecting group afforded methyl 6-(S)-acetyl-4,5-O-isopropylidene-6-thio-D-galactonate 11 in 70% yield. Saponification of compound 11 gave the 6-(S)-4,5-O-isopropylidene-6-thio-D-galactonic acid 12 in quantitative yield. Treatment of 12 with DIC/HOBt as coupling reagents gave, after cyclisation; the target compound: 4,5-O-isopropylidene 6-thio-D-galactono-1,6-lactone 13 in 49% yield. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.088