(S)-6-bromo-2-tert-butoxycarbonylamino-5-oxohexanoic acid tert-butyl ester | 220243-87-8

• 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-bromo-2-tert-butoxycarbonylamino-5-oxohexanoic acid tert-butyl ester
• 英文别名: (S)-(-)-tert-butyl-6-bromo-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate；(2S)-tert-butyl 6-bromo-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate；6-Bromo-N-[(1,1-dimethylethoxy)carbonyl]-5-oxo-L-norleucine 1,1-dimethylethyl ester；tert-butyl (2S)-6-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxohexanoate
• CAS: 220243-87-8
• 化学式: C₁₅H₂₆BrNO₅
• 分子量: 380.279
• InChiKey: MKMOASDZWHWOGH-NSHDSACASA-N

物化性质

• 沸点：
  461.8±40.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-6-bromo-2-tert-butoxycarbonylamino-5-oxohexanoic acid tert-butyl ester 在 1,1,2,3-四甲基胍 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 14.0h， 生成 (S,S)-1-allyl-4-[2-tert-butoxycarbonylamino-2-(tert-butoxycarbonyl)ethyl]-5-[3-tert-butoxycarbonylamino-3-(tert-butoxycarbonyl)propyl]pyridinium-3-olate
  参考文献：
  名称：

  A practical protocol for the synthesis of 3-hydroxy-4,5-disubstituted pyridine derivatives from acyclic compounds

  摘要：

  本文报告了一种简单的协议，通过丙烯胺或苄胺与α-溴酮反应及随后的N-去烷基化，组装3-羟基-4,5-二取代吡啶环。

  DOI：

  10.1039/b105478n
• 作为产物：
  描述：

  Boc-L-谷氨酸-1-叔丁酯 在 N-甲基吗啉 、 氢溴酸 、 百里酚蓝 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.5h， 生成 (S)-6-bromo-2-tert-butoxycarbonylamino-5-oxohexanoic acid tert-butyl ester
  参考文献：
  名称：

  A practical protocol for the synthesis of 3-hydroxy-4,5-disubstituted pyridine derivatives from acyclic compounds

  摘要：

  本文报告了一种简单的协议，通过丙烯胺或苄胺与α-溴酮反应及随后的N-去烷基化，组装3-羟基-4,5-二取代吡啶环。

  DOI：

  10.1039/b105478n

文献信息

• Bone collagen cross-links: an efficient one-pot synthesis of (+)-pyridinoline and (+)-dexoypyridinoline
  作者：Maciej Adamczyk、Donald D Johnson、Rajarathnam E Reddy

  DOI：10.1016/s0957-4166(00)00195-6

  日期：2000.6

  A one-pot reaction of (2S, 5R)-(-)-tert-butyl-[(2-tert-butoxycarbonyl)amino]-5-hydroxy-6-amino-hexanoate 2b or (S)-(-)-tert-butyl-[(2-tert-butoxycarbonyl)amino]-6-aminohexanoate 2c with (S)-(-)-tert-butyl-6-bromo-[bis-(2-tert-butoxycarbonyl)amino]-5-oxohexanoate 5 in the presence of K2CO3 in MeCN-MeOH followed by hydrolysis gave bone collagen cross-links, (+)-Pyd 1b or (+)-Dpd 1c, in 42-48% yield, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Collagen cross-links: Synthesis of pyridinoline, deoxypyridinoline and their analogues
  作者：Maciej Adamczyk、Donald D. Johnson、Rajarathnam E. Reddy

  DOI：10.1016/s0040-4020(98)01023-0

  日期：1999.1
• A simple strategy for the synthesis of the glycosylated collagen biomarkers α-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-O-pyridinoline (Glc-Gal-PYD), α-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-5-O-hydroxylysine (Glc-Gal-Hyl) and of their unnatural epimers Glc-Gal-epiPYD and Glc-Gal-epiHyl
  作者：Pietro Allevi、Eti A. Femia、Elios Giannini、Mario Anastasia

  DOI：10.1016/j.tetasy.2007.10.037

  日期：2007.11

  A short synthetic strategy for the preparation of the alpha-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-O-pyridinoline (Glc-Gat-PYD), of the alpha-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-5-O-hydroxylysine (Glc-Gal-Hyl) and of their respective epimers, Glc-Gal-epiPYD and Glc-Gal-epiHyl, useful for the analytical evaluation of collagen biomarkers in human sinovium and bone, is reported. (c) 2007 Elsevier Ltd. All rights reserved.
• Total synthesis of the collagen glycosylated cross-link β-d-galactopyranosyl-O-pyridinoline and of its unnatural epimer β-d-galactopyranosyl-O-epipyridinoline
  作者：Pietro Allevi、Raffaele Colombo、Elios Giannini、Mario Anastasia

  DOI：10.1016/j.tetasy.2007.07.006

  日期：2007.7

  A short parallel synthesis Of beta-D-galactopyranosyl-O-pyridinoline (Ga1-PYD), a collagen glycoconjugated cross-link, and of Ga1-epiPYD, a (5S)-epimer, useful as internal standard in the analytical evaluation of the natural isomer in human tissue, is reported. (c) 2007 Elsevier Ltd. All rights reserved.
• A practical protocol for the synthesis of 3-hydroxy-4,5-disubstituted pyridine derivatives from acyclic compounds
  作者：Luigi Anastasia†、Mario Anastasia、Pietro Allevi

  DOI：10.1039/b105478n

  日期：——

  The paper reports a simple protocol for assembling a 3-hydroxy-4,5-disubstituted pyridine ring by reaction of allylamine or benzylamine and an α-bromo ketone and successive N-dealkylation.

  本文报告了一种简单的协议，通过丙烯胺或苄胺与α-溴酮反应及随后的N-去烷基化，组装3-羟基-4,5-二取代吡啶环。