methyl 6-(S)-acetyl-6-deoxy-2,3:4,5-di-O-isopropylidene-6-thio-D-galactonate | 849414-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-(S)-acetyl-6-deoxy-2,3:4,5-di-O-isopropylidene-6-thio-D-galactonate
• CAS: 849414-58-0
• 化学式: C₁₅H₂₄O₇S
• 分子量: 348.417
• InChiKey: FBCZRMPJBJBUQH-NOOOWODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 6-(S)-acetyl-6-deoxy-2,3:4,5-di-O-isopropylidene-6-thio-D-galactonate 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (3R,4S,5S,6R,10R,11S,12S,13R)-2,9-dioxo-3,4:5,6;10,11:12,13-tetra-O-isopropylideneoctaoxy-1,8-dithiacyclotetradecane
  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：

  methyl 6-bromo-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以100%的产率得到methyl 6-(S)-acetyl-6-deoxy-2,3:4,5-di-O-isopropylidene-6-thio-D-galactonate
  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