tert-butyl-(S)-(-)-6-bromo-2-[bis(tert-butoxycarbonyl)amino]-5-oxohexanoate | 260552-88-3

• 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-(S)-(-)-6-bromo-2-[bis(tert-butoxycarbonyl)amino]-5-oxohexanoate
• 英文别名: (S)-(-)-tert-butyl-6-bromo-2-[bis-(tert-butoxycarbonyl)amino]-5-oxohexanoate；tert-butyl (2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-6-bromo-5-oxohexanoate
• CAS: 260552-88-3
• 化学式: C₂₀H₃₄BrNO₇
• 分子量: 480.396
• InChiKey: BDKAARDETNQHOD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl-(S)-(-)-6-bromo-2-[bis(tert-butoxycarbonyl)amino]-5-oxohexanoate 在 air 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 43.0h， 生成
  参考文献：
  名称：

  Bone collagen cross-links: an efficient one-pot synthesis of (+)-pyridinoline and (+)-dexoypyridinoline

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00195-6
• 作为产物：
  描述：

  (S)-1-tert-butyl 5-methyl 2-(bis(tert-butoxycarbonyl)amino)pentanedioate 在 N-甲基吗啉 、 氢氧化钾 、 lithium hydroxide 、 氢溴酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.17h， 生成 tert-butyl-(S)-(-)-6-bromo-2-[bis(tert-butoxycarbonyl)amino]-5-oxohexanoate
  参考文献：
  名称：

  Bone collagen cross-links: an efficient one-pot synthesis of (+)-pyridinoline and (+)-dexoypyridinoline

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00195-6

文献信息

• Synthesis of unnatural homologues of deoxypyridinoline as possible internal standards in analytical detection of pyridinolinic cross-links of collagen
  作者：Pietro Allevi、Eti Alessandra Femia、Paola Rota、Maria Letizia Costa、Mario Anastasia

  DOI：10.1016/j.tetasy.2008.11.001

  日期：2008.11

  Three homologues of the collagen cross-links deoxypyridinoline, differing in the length of the side chain at the aromatic nitrogen, have been efficiently synthesized as possible internal standards in the quantitative analyses of pyridinolines. The first has a one-carbon shorter N-chain, while other two have a one-carbon and a two-carbon longer N-chain. The stereogenic centers are introduced stereoselectively using Williams' glycine template methodology and oxazinones to generate chirality and to suitably protect the amino acid functionality during assembly of the pyridinoline nucleus. (C) 2008 Elsevier Ltd. All rights reserved.
• An efficient one-pot synthesis of (+)-deoxypyridinoline
  作者：Maciej Adamczyk、Donald D. Johnson、Rajarathnam E. Reddy

  DOI：10.1016/s0040-4039(99)01936-x

  日期：1999.12

  An efficient one-pot synthesis of (+)-deoxypyridinoline (Dpd, 1), the cross-link of bone collagen, was achieved from tert-butyl-(S)-(-)-[(2-tert-butoxycarbonyl)amino]-6-aminohexanoate (2) and tert-butyl-(S)-(-)-6-bromo-2-[bis(tert-butoxycarbonyl)amino]-5-oxohexanoate (3) in 42% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.