(+)-5-(benzyloxy)-4-{[(2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-2-pyrazinyl]methyl}nicotinaldehyde | 252987-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (+)-5-(benzyloxy)-4-{[(2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-2-pyrazinyl]methyl}nicotinaldehyde
• 英文别名: 4-[[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]methyl]-5-phenylmethoxypyridine-3-carbaldehyde
• CAS: 252987-10-3
• 化学式: C₂₃H₂₇N₃O₄
• 分子量: 409.485
• InChiKey: XFUMOIBOTGDPLO-PZJWPPBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-5-(benzyloxy)-4-{[(2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-2-pyrazinyl]methyl}nicotinaldehyde 在 palladium on activated charcoal 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 正丁基锂 、 氢气 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， -78.0~20.0 ℃ 、137.9 kPa 条件下， 反应 17.25h， 生成 (-)-methyl-(2S)-2-[bis(tert-butoxycarbonyl)amino]-3-(3-{(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}-5-hydroxy-4-pyridinyl)propanoate
  参考文献：
  名称：

  Versatile synthesis of (+)-deoxypyridinoline, a biochemical marker for diagnosis of osteoporosis

  摘要：

  A versatile chiral synthesis of the bone collagen cross-link, (+)-deoxypyridinoline (Dpd, 1) was described starting from a 3-hydroxypyridine derivative (2) via sequential introduction of three amino acid chains followed by hydrolysis. The key synthon 2, was prepared from vitamin B-6 (6). (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00329-8
• 作为产物：
  描述：

  5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carbaldehyde 在 盐酸 、 manganese(IV) oxide 、 氢氧化钾 、 正丁基锂 、 氯化亚砜 、 乙醇 、 sodium ethanolate 、 4-甲基苯磺酸吡啶 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 xylene 、 苯 为溶剂， 反应 117.92h， 生成 (+)-5-(benzyloxy)-4-{[(2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-2-pyrazinyl]methyl}nicotinaldehyde
  参考文献：
  名称：

  Versatile synthesis of (+)-deoxypyridinoline, a biochemical marker for diagnosis of osteoporosis

  摘要：

  A versatile chiral synthesis of the bone collagen cross-link, (+)-deoxypyridinoline (Dpd, 1) was described starting from a 3-hydroxypyridine derivative (2) via sequential introduction of three amino acid chains followed by hydrolysis. The key synthon 2, was prepared from vitamin B-6 (6). (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00329-8

文献信息

• Transformation of Vitamin B6 to (+)-Deoxypyridinoline, a useful Biochemical Marker for Diagnosis of Bone Diseases
  作者：Maciej Adamczyk、Srinivasa Rao Akireddy、Rajarathnam E. Reddy

  DOI：10.1016/s0040-4020(00)00121-6

  日期：2000.4

  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.
• Versatile synthesis of (+)-deoxypyridinoline, a biochemical marker for diagnosis of osteoporosis
  作者：Maciej Adamczyk、Srinivasa Rao Akireddy、Rajarathnam E. Reddy

  DOI：10.1016/s0957-4166(99)00329-8

  日期：1999.8

  A versatile chiral synthesis of the bone collagen cross-link, (+)-deoxypyridinoline (Dpd, 1) was described starting from a 3-hydroxypyridine derivative (2) via sequential introduction of three amino acid chains followed by hydrolysis. The key synthon 2, was prepared from vitamin B-6 (6). (C) 1999 Published by Elsevier Science Ltd. All rights reserved.