(3R,4R,5S,6R)-6-Dimethoxymethyl-3-methyl-4,5-bis-trifluoromethanesulfonyloxy-[1,2]oxazinane-2-carboxylic acid benzyl ester | 173602-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R,5S,6R)-6-Dimethoxymethyl-3-methyl-4,5-bis-trifluoromethanesulfonyloxy-[1,2]oxazinane-2-carboxylic acid benzyl ester
• CAS: 173602-42-1
• 化学式: C₁₈H₂₁F₆NO₁₁S₂
• 分子量: 605.487
• InChiKey: NTHLTDHNMGZUGM-FMKGYKFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  143.97
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S,6R)-6-Dimethoxymethyl-3-methyl-4,5-bis-trifluoromethanesulfonyloxy-[1,2]oxazinane-2-carboxylic acid benzyl ester 在 palladium on activated charcoal barium dihydroxide 、 二氧化硫 、 氢气 、 苯酸四丁基铵 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 47.0h， 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：

  三氟甲磺酸酐 、 benzyl (3R,4R,5R,6R)-6-(dimethoxymethyl)-4,5-dihydroxy-3-methyloxazinane-2-carboxylate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到(3R,4R,5S,6R)-6-Dimethoxymethyl-3-methyl-4,5-bis-trifluoromethanesulfonyloxy-[1,2]oxazinane-2-carboxylic acid benzyl ester
  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