(-)-methyl-(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-{(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}-5-hydroxy-4-pyridinyl)propanoate | 252987-14-7

• 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: (-)-methyl-(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-{(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}-5-hydroxy-4-pyridinyl)propanoate
• 英文别名: methyl (2S)-3-[3-hydroxy-5-[(3S)-4-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]pyridin-4-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 252987-14-7
• 化学式: C₂₃H₃₇N₃O₈
• 分子量: 483.562
• InChiKey: IKMRSHLATBUZDQ-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  156
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (-)-methyl-(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-{(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}-5-hydroxy-4-pyridinyl)propanoate 在 chromium(VI) oxide 、 硫酸 作用下， 以 1,4-二氧六环 、 甲醇 、 丙酮 、 苯 为溶剂， 反应 4.92h， 生成 tert-butyl (2S)-6-[3-hydroxy-5-[(3S)-4-methoxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutyl]-4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]pyridin-1-ium-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate;iodide
  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：

  3-Benzyloxy-4-chloromethyl-5-(4-methoxy-benzyloxymethyl)-pyridine 在 palladium on activated charcoal 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 正丁基锂 、 氢气 、 caesium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， -78.0~20.0 ℃ 、137.9 kPa 条件下， 反应 83.25h， 生成 (-)-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：

  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.