(S)-2-glutarsaeure-1-(tert-butyl)ester | 129241-87-8

• 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)-2-glutarsaeure-1-(tert-butyl)ester
• 英文别名: α-tert-butyl N,N-di-(tert-butoxycarbonyl)-L-glutamate；(S)-5-butoxy-4-[bis-(tert-butoxycarbonyl)amino]-5-oxopentanoic acid；N,N-Bis(tert-butoxycarbonyl)-L-glutamic acid α-tert-butyl ester；N(Boc2)Glu-OtBu；(4S)-4-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
• CAS: 129241-87-8
• 化学式: C₁₉H₃₃NO₈
• 分子量: 403.473
• InChiKey: PMWDEWNEFUNWTF-LBPRGKRZSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  490.9±55.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2-glutarsaeure-1-(tert-butyl)ester 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 10.0~25.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 tert-butyl (2S)-2-{bis[(tert-butoxy)carbonyl]amino}-5-oxopentanoate
  参考文献：
  名称：

  Herstellung von'Semialdehyd'-Derivaten vonAsparaginsäure-和Glutaminsäuredurch Rosenmund-还原

  摘要：

  天门冬氨酸和谷氨酸的“半醛”衍生物的制备通过的罗森蒙德减少

  DOI：

  10.1002/hlca.19900730219
• 作为产物：
  描述：

  (S)-1-tert-butyl 5-methyl 2-(bis(tert-butoxycarbonyl)amino)pentanedioate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-2-glutarsaeure-1-(tert-butyl)ester
  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

• ENZYME AND RECEPTOR MODULATION
  申请人：Davidson Alan Hornsby

  公开号：US20100317865A1

  公开（公告）日：2010-12-16

  Covalent conjugates of an α,α-disubstituted glycine ester and a modulator of the activity of a target intracellular enzyme or receptor, wherein the ester group of the conjugate is hydrolysable by one or more intracellular carboxylesterase enzymes to the corresponding acid and the α,α-disubstituted glycine ester is conjugated to the modulator at a position remote from the binding interface between the inhibitor and the target enzyme or receptor pass into cells and the active acid hydrolysis product accumulates within the cells.

  一种α，α-二取代甘氨酸酯和靶细胞内酶或受体活性调节剂的共价结合物，其中共轭物的酯基可被一个或多个细胞内羧酯酶水解为相应的酸，α，α-二取代甘氨酸酯与调节剂结合在远离抑制剂与靶酶或受体之间结合界面的位置，进入细胞并使活性酸水解产物在细胞内积累。
• The efficient, enantioselective synthesis of quinoxaline, pyrazine and 1,2,4-triazine substituted α-amino acids from vicinal tricarbonyls
  作者：Robert M. Adlington、Jack E. Baldwin、David Catterick、Gareth J. Pritchard

  DOI：10.1039/b010134f

  日期：——

  The reaction of diamines and amidrazones with α-amino acid vicinal tricarbonyls has been shown to be a versatile route towards novel heterocyclic α-amino acids. This route is also applicable to parallel synthesis and has allowed the formation of a range of heterocyclic amino acid systems.

  二胺和脒酮与δ±-氨基酸邻位三羰基的反应已被证明是一种获得新型杂环δ±-氨基酸的多功能途径。这条路线也适用于平行合成，并可形成一系列杂环氨基酸体系。
• Convenient Preparation of α-Tert-Butyl N-Blocked Glutamates Through γ-Allyl Ester Protection
  作者：V. Bavetsias、G. M. F. Bisset、M. Jarman

  DOI：10.1080/00397919508012656

  日期：1995.4

  Abstract Utilisation of γ-allyl ester protection of glutamates provides a convenient route to the synthesis of Z-Glu-OBut, Tr-Glu-OBut and (Boc)2-Glu-OBut.

  摘要 利用谷氨酸的γ-烯丙基酯保护为合成Z-Glu-OBut、Tr-Glu-OBut和(Boc)2-Glu-OBut提供了一条便捷的途径。
• A versatile synthetic route to quinoxaline, pyrazine and 1,2,4-triazine substituted α-amino acids from vicinal tricarbonyls
  作者：Robert M. Adlington、Jack E. Baldwin、David Catterick、Gareth J. Pritchard

  DOI：10.1039/a909722h

  日期：——

  A range of novel heterocyclic α-amino acids has been synthesised by the reaction of diamines and amidrazones with α-amino acid vicinal tricarbonyl reactive substrates.

  通过下列反应合成了一系列新的杂环α-氨基酸。 二胺 酰胺基与α-氨基酸邻位三羰基反应性底物。
• Asymmetric synthesis of differentially protected meso-2,6-diaminopimelic acid
  作者：John L. Roberts、Cecil Chan

  DOI：10.1016/s0040-4039(02)01844-0

  日期：2002.10

  meso-2,6-Diaminopimelic acid, an important linking component of bacterial cell walls and a biosynthetic precursor of L-lysine has been prepared differentially protected in a stereospecific manner from both L-aspartic and L-glutamic acid. The key step to establish the second chiral center involves the asymmetric reduction of a pyruvate moiety with Alpine-Borane(R). S-2-Amino-6-oxopimelic acid, the hydrolyzed open chain form of tetrahydrodipicolinic acid, a biosynthetic precursor of meso-2,6-diaminopimelic acid, was also prepared via deprotection of the key pyruvate intermediate. (C) 2002 Elsevier Science Ltd. All rights reserved.