(+)-4-N-acetylamino-5-(hydroxymethyl)cyclopentene-3,5-diol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-4-N-acetylamino-5-(hydroxymethyl)cyclopentene-3,5-diol
• 英文别名: N-[(1R,2R,5S)-2,5-dihydroxy-2-(hydroxymethyl)cyclopent-3-en-1-yl]acetamide
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: GHGQQBCENXNGRG-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-4-N-acetylamino-5-(hydroxymethyl)cyclopentene-3,5-diol 在 吡啶 、 混旋樟脑磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.5h， 生成 [(5R,8S,9R)-9-acetamido-2,2-dimethyl-1,3-dioxaspiro[4.4]non-6-en-8-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Pyridinium Salt Photochemistry in a Concise Route for Synthesis of the Trehazolin Aminocyclitol, Trehazolamine

  摘要：

  A strategy for the concise synthesis of trehazolamine, the aminocyclitol core of the potent trehalase inhibitor trehazolin, has been developed. The methodology takes advantage of photocyclization reaction of 1-methoxyethoxymethyl-3-pivaloxymethylpyridinium perchlorate to generate a bicyclicaziridine intermediate, which is transformed under aziridine ring opening conditions to the key intermediate, 3,5-diacetoxy-3-pivaloxymethyl-4-(N-acetylamino)cyclopentene. In addition, the strategy is used in an enantio-divergent sequence for preparation of the natural (+)-trehazolamine and its unnatural (-)-enantiomer. In this route, the chiral auxiliary containing 1-(tetracetyl-alpha-D-glucosyl)-3-pivaloxymethylpyridinium perchlorate undergoes photocyclization to generate separable, diastereomeric bicyclic-aziridines, which are then independently transformed to enantiomeric 3,5diacetoxy-3-pivaloxymethyl-4-(N-acetylamino)cyclopentenes.

  DOI：

  10.1021/jo050589q
• 作为产物：
  描述：

  3-吡啶甲醇 在 盐酸 、 TEA 、 sodium methylate 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 60.0 ℃ 、1.6 kPa 条件下， 反应 57.0h， 生成 (+)-4-N-acetylamino-5-(hydroxymethyl)cyclopentene-3,5-diol
  参考文献：
  名称：

  Pyridinium Salt Photochemistry in a Concise Route for Synthesis of the Trehazolin Aminocyclitol, Trehazolamine

  摘要：

  A strategy for the concise synthesis of trehazolamine, the aminocyclitol core of the potent trehalase inhibitor trehazolin, has been developed. The methodology takes advantage of photocyclization reaction of 1-methoxyethoxymethyl-3-pivaloxymethylpyridinium perchlorate to generate a bicyclicaziridine intermediate, which is transformed under aziridine ring opening conditions to the key intermediate, 3,5-diacetoxy-3-pivaloxymethyl-4-(N-acetylamino)cyclopentene. In addition, the strategy is used in an enantio-divergent sequence for preparation of the natural (+)-trehazolamine and its unnatural (-)-enantiomer. In this route, the chiral auxiliary containing 1-(tetracetyl-alpha-D-glucosyl)-3-pivaloxymethylpyridinium perchlorate undergoes photocyclization to generate separable, diastereomeric bicyclic-aziridines, which are then independently transformed to enantiomeric 3,5diacetoxy-3-pivaloxymethyl-4-(N-acetylamino)cyclopentenes.

  DOI：

  10.1021/jo050589q

文献信息

• Pyridinium Salt Photochemistry in a Concise Route for Synthesis of the Trehazolin Aminocyclitol, Trehazolamine
  作者：Xiaohua Feng、Eileen N. Duesler、Patrick S. Mariano

  DOI：10.1021/jo050589q

  日期：2005.7.1

  A strategy for the concise synthesis of trehazolamine, the aminocyclitol core of the potent trehalase inhibitor trehazolin, has been developed. The methodology takes advantage of photocyclization reaction of 1-methoxyethoxymethyl-3-pivaloxymethylpyridinium perchlorate to generate a bicyclicaziridine intermediate, which is transformed under aziridine ring opening conditions to the key intermediate, 3,5-diacetoxy-3-pivaloxymethyl-4-(N-acetylamino)cyclopentene. In addition, the strategy is used in an enantio-divergent sequence for preparation of the natural (+)-trehazolamine and its unnatural (-)-enantiomer. In this route, the chiral auxiliary containing 1-(tetracetyl-alpha-D-glucosyl)-3-pivaloxymethylpyridinium perchlorate undergoes photocyclization to generate separable, diastereomeric bicyclic-aziridines, which are then independently transformed to enantiomeric 3,5diacetoxy-3-pivaloxymethyl-4-(N-acetylamino)cyclopentenes.