(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-methyl-piperidine-2-sulfonic acid | 173829-16-8

• 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,4S,5S,6R)-3,4,5-Trihydroxy-6-methyl-piperidine-2-sulfonic acid
• 英文别名: (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylpiperidine-2-sulfonic acid
• CAS: 173829-16-8
• 化学式: C₆H₁₃NO₆S
• 分子量: 227.238
• InChiKey: YYBFBMWRCGDISH-PHYPRBDBSA-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,4S,5S,6R)-3,4,5-Trihydroxy-6-methyl-piperidine-2-sulfonic acid 在 palladium on activated charcoal barium dihydroxide 、 氢气 作用下， 生成 1,5,6-trideoxy-1,5-imino-D-galactitol
  参考文献：
  名称：

  6-Deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and d-series, d-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions

  摘要：

  Nucleophilic ring opening of the cyclic sulfates (+/-)-9c and D-9c and of the epoxide (+/-)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder adduct of hexadienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy-nojirimycin and its isomers are mixtures of alpha- and beta-anomers and of the corresponding imine. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00898-3
• 作为产物：
  描述：

  benzyl (3R,4R,5R,6R)-6-(dimethoxymethyl)-4,5-dihydroxy-3-methyloxazinane-2-carboxylate 在 palladium on activated charcoal 吡啶 、 二氧化硫 、 氢气 、 苯酸四丁基铵 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 37.0h， 生成 (2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-methyl-piperidine-2-sulfonic acid
  参考文献：
  名称：

  6-Deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and d-series, d-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions

  摘要：

  Nucleophilic ring opening of the cyclic sulfates (+/-)-9c and D-9c and of the epoxide (+/-)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder adduct of hexadienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy-nojirimycin and its isomers are mixtures of alpha- and beta-anomers and of the corresponding imine. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00898-3

文献信息

• 6-Deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and d-series, d-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions
  作者：Albert Defoin、Hervé Sarazin、Jacques Streith

  DOI：10.1016/s0040-4020(97)00898-3

  日期：1997.10

  Nucleophilic ring opening of the cyclic sulfates (+/-)-9c and D-9c and of the epoxide (+/-)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder adduct of hexadienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy-nojirimycin and its isomers are mixtures of alpha- and beta-anomers and of the corresponding imine. (C) 1997 Elsevier Science Ltd.