(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methylpiperidine-2-sulfonic acid | 173829-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methylpiperidine-2-sulfonic acid
• CAS: 173829-15-7
• 化学式: C₆H₁₃NO₆S
• 分子量: 227.238
• InChiKey: YYBFBMWRCGDISH-UKFBFLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methylpiperidine-2-sulfonic acid 在 palladium on activated charcoal barium dihydroxide 、 氢气 作用下， 生成 5-amino-1,5,6-trideoxy-D-allose
  参考文献：
  名称：

  6-Deoxy-allo-nojirimycin in the racemic and d-series, 6-deoxy-d,l-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-d,l-allosamine via hetero-Diels-Alder cycloadditions

  摘要：

  Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cycloadducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6-deoxy-2-D,L-allosamine 15b, to 6-deoxy-D,L and D-allo-nojirimycin 15a, D-15a, to 6-deoxy-D,L-talo-nojirimycin 15c as well as to their l-deoxy-derivatives 16a, D-16a, 16c via their crystalline l-deoxy-l-sulfonic acid derivatives (sulfite adducts). Amino-sugars 16a,c are mixtures of alpha- and -beta-anomers and of the corresponding imines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00897-1
• 作为产物：
  描述：

  sorbaldehyde dimethylacetal 在 palladium on activated charcoal 四氧化锇 、 N-甲基吲哚酮 、 甲酸甲酯 、 1-deoxy-2,3:5,6-di-O-isopropylidene-1-nitroso-α-D-mannofutanosyl chloride 、 二氧化硫 、 氢气 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 243.0h， 生成 (2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methylpiperidine-2-sulfonic acid
  参考文献：
  名称：

  6-Deoxy-allo-nojirimycin in the racemic and d-series, 6-deoxy-d,l-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-d,l-allosamine via hetero-Diels-Alder cycloadditions

  摘要：

  Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cycloadducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6-deoxy-2-D,L-allosamine 15b, to 6-deoxy-D,L and D-allo-nojirimycin 15a, D-15a, to 6-deoxy-D,L-talo-nojirimycin 15c as well as to their l-deoxy-derivatives 16a, D-16a, 16c via their crystalline l-deoxy-l-sulfonic acid derivatives (sulfite adducts). Amino-sugars 16a,c are mixtures of alpha- and -beta-anomers and of the corresponding imines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00897-1