(3S,4R,5S)-6-(4-Bromo-benzyloxy)-3,4,5-trihydroxy-hexanoic acid methoxy-methyl-amide | 1053643-71-2

• 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: (3S,4R,5S)-6-(4-Bromo-benzyloxy)-3,4,5-trihydroxy-hexanoic acid methoxy-methyl-amide
• 英文别名: (3S,4R,5S)-6-[(4-bromophenyl)methoxy]-3,4,5-trihydroxy-N-methoxy-N-methylhexanamide
• CAS: 1053643-71-2
• 化学式: C₁₅H₂₂BrNO₆
• 分子量: 392.247
• InChiKey: CQECNZMSLHBSGC-KCQAQPDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  99.5
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-6-(4-Bromo-benzyloxy)-3,4,5-trihydroxy-hexanoic acid methoxy-methyl-amide 在 吡啶 、 正丁基锂 、 对甲苯磺酸 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 生成 (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(tert-butyldimethyl)oxy>-1-(1,3-dithia-2-cyclohexyl)-1-cyclohexanone
  参考文献：
  名称：

  Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative

  摘要：

  The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a noncarbohydrate precursor was achieved in six steps (19% yield) from a chiral, gamma,delta-epoxy beta-hydroxy ester, 3a, readily available from the corresponding alpha,beta-epoxy aldehyde. The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.

  DOI：

  10.1021/jo00127a047
• 作为产物：
  描述：

  (S)-3-[(2S,3S)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-hydroxy-propionic acid tert-butyl ester 在 三甲基氯硅烷 、 三甲基铝 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 12.53h， 生成 (3S,4R,5S)-6-(4-Bromo-benzyloxy)-3,4,5-trihydroxy-hexanoic acid methoxy-methyl-amide
  参考文献：
  名称：

  Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative

  摘要：

  The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a noncarbohydrate precursor was achieved in six steps (19% yield) from a chiral, gamma,delta-epoxy beta-hydroxy ester, 3a, readily available from the corresponding alpha,beta-epoxy aldehyde. The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.

  DOI：

  10.1021/jo00127a047

文献信息

• Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative
  作者：Gerard Devianne、Jean-Marc Escudier、Michel Baltas、Liliane Gorrichon

  DOI：10.1021/jo00127a047

  日期：1995.11

  The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a noncarbohydrate precursor was achieved in six steps (19% yield) from a chiral, gamma,delta-epoxy beta-hydroxy ester, 3a, readily available from the corresponding alpha,beta-epoxy aldehyde. The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.