(2R,4R,5R)-2-<(tert-butoxycarbonyl)amino>-5,6-dihydroxyhexan-4-olide | 149775-97-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,4R,5R)-2-<(tert-butoxycarbonyl)amino>-5,6-dihydroxyhexan-4-olide
• CAS: 149775-97-3
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: UBXXPKZNCFPCOX-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  105.09
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (2R,4R,5R)-2-<(tert-butoxycarbonyl)amino>-5,6-dihydroxyhexan-4-olide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到(2R,4R,5R)-2-<(tert-butoxycarbonyl)amino>-6-(tert-butyldimethylsiloxy)-5-hydroxyhexan-4-olide
  参考文献：
  名称：

  Short, stereoselective syntheses of 4,5,6-trihydroxylated norleucines: An approach to the synthesis of (+)-bulgecinine

  摘要：

  Reaction of the L-serine derived zinc reagent 1 with D-isopropylideneglyceryl chloride gave the 4-oxo amino acid 5, which was reduced with high diastereoselectivity to give the trans-lactone 7. Analogous reaction of the D-serine derived zinc reagent gave the the 4-oxo amino acid 6, which was reduced with high diastereoselectivity to give the cis-lactone 8. Conversion of 8 to 11, the enantiomer of the Boc-protected analogue 10 of an intermediate in Fleet's synthesis of (-)-bulgecinine, was achieved in two steps.

  DOI：

  10.1016/s0040-4039(00)60500-2
• 作为产物：
  描述：

  benzyl (2R,5R)-2-<(tert-butoxycarbonyl)amino>-5,6-isopropylidenedioxy-4-oxohexanoate 在 碘 、 L-Selectride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 51.0h， 生成 (2R,4R,5R)-2-<(tert-butoxycarbonyl)amino>-5,6-dihydroxyhexan-4-olide
  参考文献：
  名称：

  Short, stereoselective syntheses of 4,5,6-trihydroxylated norleucines: An approach to the synthesis of (+)-bulgecinine

  摘要：

  Reaction of the L-serine derived zinc reagent 1 with D-isopropylideneglyceryl chloride gave the 4-oxo amino acid 5, which was reduced with high diastereoselectivity to give the trans-lactone 7. Analogous reaction of the D-serine derived zinc reagent gave the the 4-oxo amino acid 6, which was reduced with high diastereoselectivity to give the cis-lactone 8. Conversion of 8 to 11, the enantiomer of the Boc-protected analogue 10 of an intermediate in Fleet's synthesis of (-)-bulgecinine, was achieved in two steps.

  DOI：

  10.1016/s0040-4039(00)60500-2

文献信息

• Jackson, Richard F. W.; Rettie, Alan B.; Wood, Anthony, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1719 - 1726
  作者：Jackson, Richard F. W.、Rettie, Alan B.、Wood, Anthony、Withes, Martin J.

  DOI：——

  日期：——