(S)-(-)-[(6)-13CD2]-1-tert-butyl-2-[(tert-butoxycarbonyl)amino]-6-hydroxyhexanoate | 282107-35-1

• 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: (S)-(-)-[(6)-13CD2]-1-tert-butyl-2-[(tert-butoxycarbonyl)amino]-6-hydroxyhexanoate
• 英文别名: tert-butyl (2S)-6,6-dideuterio-6-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino](613C)hexanoate
• CAS: 282107-35-1
• 化学式: C₁₅H₂₉NO₅
• 分子量: 306.372
• InChiKey: QGRZGCDRSJDGOA-GIAYTSOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(-)-[(6)-13CD2]-1-tert-butyl-2-[(tert-butoxycarbonyl)amino]-6-hydroxyhexanoate 在 咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到(S)-(-)-[(6)-13CD2]-1-tert-butyl-2-[(tert-butoxycarbonyl)amino]-6-iodohexanoate
  参考文献：
  名称：

  Synthesis of isotopically labeled (+)-deoxypyridinoline

  摘要：

  An efficient synthesis of isotopically labeled (+)-deoxypyridinoline ((3) under bar) was achieved via quaternization of (S,S)-(-)-(4) under bar with (S)-(-)-iodide ((5) under bar) and subsequent hydrolysis. The required (S)-(-)-iodide ((5) under bar) was prepared from a commercially available (S)-5-(tert-butoxy)-4-[(tert-butoxycarbonyl)amino]-5- oxopentanoic acid ((6) under bar) in seven steps and good overall yield.

  DOI：

  10.1002/(sici)1099-1344(200004)43:5<463::aid-jlcr332>3.0.co;2-y
• 作为产物：
  描述：

  tert-butyl (2S)-2-{bis[(tert-butoxy)carbonyl]amino}-5-oxopentanoate 在 正丁基锂 、 硼烷四氢呋喃络合物 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 34.75h， 生成 (S)-(-)-[(6)-13CD2]-1-tert-butyl-2-[(tert-butoxycarbonyl)amino]-6-hydroxyhexanoate
  参考文献：
  名称：

  Synthesis of isotopically labeled (+)-deoxypyridinoline

  摘要：

  An efficient synthesis of isotopically labeled (+)-deoxypyridinoline ((3) under bar) was achieved via quaternization of (S,S)-(-)-(4) under bar with (S)-(-)-iodide ((5) under bar) and subsequent hydrolysis. The required (S)-(-)-iodide ((5) under bar) was prepared from a commercially available (S)-5-(tert-butoxy)-4-[(tert-butoxycarbonyl)amino]-5- oxopentanoic acid ((6) under bar) in seven steps and good overall yield.

  DOI：

  10.1002/(sici)1099-1344(200004)43:5<463::aid-jlcr332>3.0.co;2-y

文献信息

• Synthesis of isotopically labeled (+)-deoxypyridinoline
  作者：Maciej Adamczyk、Donald D. Johnson、Rajarathnam E. Reddy、Sushil D. Rege

  DOI：10.1002/(sici)1099-1344(200004)43:5<463::aid-jlcr332>3.0.co;2-y

  日期：2000.4

  An efficient synthesis of isotopically labeled (+)-deoxypyridinoline ((3) under bar) was achieved via quaternization of (S,S)-(-)-(4) under bar with (S)-(-)-iodide ((5) under bar) and subsequent hydrolysis. The required (S)-(-)-iodide ((5) under bar) was prepared from a commercially available (S)-5-(tert-butoxy)-4-[(tert-butoxycarbonyl)amino]-5- oxopentanoic acid ((6) under bar) in seven steps and good overall yield.