tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate | 280762-64-3

• 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: tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 280762-64-3
• 化学式: C₃₁H₃₉N₃O₉
• 分子量: 597.665
• InChiKey: ROEDXFBZJBFMTQ-UPVQGACJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  142.59
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate 在 palladium on activated charcoal lithium carbonate 、 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、137.89 kPa 条件下， 反应 20.0h， 以53%的产率得到(-)-methyl-(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-{(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}-5-hydroxy-4-pyridinyl)propanoate
  参考文献：
  名称：

  Transformation of Vitamin B6 to (+)-Deoxypyridinoline, a useful Biochemical Marker for Diagnosis of Bone Diseases

  摘要：

  A versatile chiral synthesis of the cross-link (+)deoxypyridinoline (Dpd, 2) was achieved starting from vitamin B-6 (7). The key steps in the synthesis of (+)-2 are transformation of B-6 (7) to the chloride (3d) and construction of three cw-amino acid chains by utilizing (R)-(-)-Schollkopf's reagent (4), Wittig reagent (R)-(-)-5, and iodide (S)-(-)-6. (+)-Dpd (2) is a degradation product of bone collagen and has been found to be a useful marker for diagnosis of osteoporosis and other metabolic bone diseases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00121-6
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{[(2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-2-pyrazinyl]methyl}-3-pyridinyl)ethenyl]-1,3-oxazolidin-2-one 在 盐酸 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 52.75h， 以46%的产率得到tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Transformation of Vitamin B6 to (+)-Deoxypyridinoline, a useful Biochemical Marker for Diagnosis of Bone Diseases

  摘要：

  A versatile chiral synthesis of the cross-link (+)deoxypyridinoline (Dpd, 2) was achieved starting from vitamin B-6 (7). The key steps in the synthesis of (+)-2 are transformation of B-6 (7) to the chloride (3d) and construction of three cw-amino acid chains by utilizing (R)-(-)-Schollkopf's reagent (4), Wittig reagent (R)-(-)-5, and iodide (S)-(-)-6. (+)-Dpd (2) is a degradation product of bone collagen and has been found to be a useful marker for diagnosis of osteoporosis and other metabolic bone diseases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00121-6