N_α,N_ξ-di-Cbz-L-lysine ethyl ester | 83173-67-5

• 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: N_α,N_ξ-di-Cbz-L-lysine ethyl ester
• 英文别名: ethyl N²,N⁶-di-Cbz-L-lysinate；Nα-Cbz-L-Lys(Nζ-Cbz)OEt；ethyl (2S)-2,6-bis(phenylmethoxycarbonylamino)hexanoate
• CAS: 83173-67-5
• 化学式: C₂₄H₃₀N₂O₆
• 分子量: 442.512
• InChiKey: NZKXICXBVQOYML-NRFANRHFSA-N

物化性质

• 沸点：
  617.1±55.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N_α,N_ξ-di-Cbz-L-lysine ethyl ester 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 20.0h， 以89%的产率得到N,N-bis-Cbz-L-lysinol
  参考文献：
  名称：

  [V2Cl3(THF)6]2[Zn2Cl6] 对 2-[N-(烷氧基羰基)氨基]醛和脂肪族醛的频哪醇交叉偶联。syn,syn-3-[N-(烷氧基羰基)氨基] 1,2-二醇的合成

  摘要：

  将 2-[N-(烷氧基羰基) 氨基] 醛缓慢加入 [V 2 Cl 3 (THF) 6 ] 2 [Zn 2 Cl 6 ] 和脂肪族醛的混合物中，得到 syn,syn-3-[N-(烷氧基羰基)氨基] 1,2-二醇，收率高，对映体纯度高 (>99:1)。N-烷氧基羰基的烷基显示出影响产率：Me>烯丙基>Bn>t-Bu。除了 N-Cbz-丙氨醛 (10:1:1)、O-苄基-N-Cbz-丝氨酸 (7:1) 和 N-Cbz-脯氨酸 (5:1 到 12:1)。一种新的丝氨酸衍生物，N-Cbz-O-TBS-丝氨酸，与正十五醛交叉偶联得到木-DC 18-植物鞘氨醇的衍生物

  DOI：

  10.1021/ja00083a017
• 作为产物：
  描述：

  L-lysine ethyl ester dihydrochloride 、 氯甲酸苄酯 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 20.0h， 以14.00 g的产率得到N_α,N_ξ-di-Cbz-L-lysine ethyl ester
  参考文献：
  名称：

  [V2Cl3(THF)6]2[Zn2Cl6] 对 2-[N-(烷氧基羰基)氨基]醛和脂肪族醛的频哪醇交叉偶联。syn,syn-3-[N-(烷氧基羰基)氨基] 1,2-二醇的合成

  摘要：

  将 2-[N-(烷氧基羰基) 氨基] 醛缓慢加入 [V 2 Cl 3 (THF) 6 ] 2 [Zn 2 Cl 6 ] 和脂肪族醛的混合物中，得到 syn,syn-3-[N-(烷氧基羰基)氨基] 1,2-二醇，收率高，对映体纯度高 (>99:1)。N-烷氧基羰基的烷基显示出影响产率：Me>烯丙基>Bn>t-Bu。除了 N-Cbz-丙氨醛 (10:1:1)、O-苄基-N-Cbz-丝氨酸 (7:1) 和 N-Cbz-脯氨酸 (5:1 到 12:1)。一种新的丝氨酸衍生物，N-Cbz-O-TBS-丝氨酸，与正十五醛交叉偶联得到木-DC 18-植物鞘氨醇的衍生物

  DOI：

  10.1021/ja00083a017

文献信息

• Enzymic Synthesis of the Delicious Peptide Fragments in Eutectic Mixtures
  作者：Xavier Jorba、Iqbal Gill、Evgeny N. Vulfson

  DOI：10.1021/jf00057a040

  日期：1995.9

  The feasibility of flavor peptide production has been investigated using proteases in liquid/semiliquid eutectic mixtures comprised of the substrates together with small amounts of water and alcohols (19-24% w/w). The three functional fragments of the so-called ''Delicious Octapeptide'', L-Lys-Gly, L-Asp-Glu-Glu, and L-Ser-Leu-Ala, were obtained in good yields without any requirement for the regioselective side-chain protection of multifunctional amino acids. The peptides were synthesized on a preparative scale in overall yields of 29-77% and were fully characterized.
• Gill, Iqbal; López-Fandiño, Rosina; Vulfson, Evgeny, Journal of the American Chemical Society, 1995, vol. 117, # 23, p. 6175 - 6177
  作者：Gill, Iqbal、López-Fandiño, Rosina、Vulfson, Evgeny

  DOI：——

  日期：——
• Pilot-Scale Enzymatic Synthesis of Bioactive Oligopeptides in Eutectic-Based Media
  作者：Iqbal Gill、Rao Valivety

  DOI：10.1021/op025528y

  日期：2002.9.1

  The bioactive peptide precursors N-alpha-Cbz-L-Lys(N-zeta-Cbz)-Gly-OEt (1), N-alpha-Cbz-L-Lys(N-zeta-Cbz)-Gly-L-Asp(OAII)-OAII (2), and N-alpha-Cbz-L-Lys(N-zeta-Cbz)-Gly-L-Asp(OAII)-L-Glu(OAII)OEt (3) were synthesized via a sequential N-to-C strategy in heterogeneous solid-liquid mixtures of substrates using Celite-deposited chymopapain and subtilisin as catalysts. The substrate pairs displayed eutectic formation, and in the presence of 16-20% w/w of water and ethanol furnished low-melting point systems that provided substrate concentrations of 0.81-1.01 M, and sustained protease catalysis. The di-, tri-, and tetra-peptide were obtained in yields of 73, 74, and 67% (yield per step) respectively, and product concentrations of 0.34, 0.48, and 0.45 g per gram of reaction mixture were achieved with these systems. The syntheses were scaled up using wiped-blade and rotating-drum reactors, and 1, 2, and 3 were produced in yields of 71, 73, and 71 %, at product concentrations of 0.36, 0.49, and 0.48 kg kg(-1), on a reaction scale of 11.34, 6.30, and 5.83 kg (11.54, 6.17, and 4.96 mol), respectively. The corresponding space-time yields were 0.30, 0.64, and 0.30 kg kg(-1) d(-1), and biocatalyst reuse provided productivities of 166, 235, and 312 kg-product kg-enzyme(-1). Furthermore, a sequential one-pot, three-step protocol was readily applied to the synthesis of the tetrapeptide 3 which was obtained with an overall yield of 34%, product concentration of 0.25 kg per kg, and space-time yield of 0.07 kg kg(-1) d(-1).
• Pinacol Cross Coupling of 2-[N-(Alkoxycarbonyl)amino] Aldehydes and Aliphatic Aldehydes by [V2Cl3(THF)6]2[Zn2Cl6]. Synthesis of syn,syn-3-[N-(Alkoxycarbonyl)amino] 1,2-Diols
  作者：Andrei W. Konradi、Scott J. Kemp、Steven F. Pedersen

  DOI：10.1021/ja00083a017

  日期：1994.2

  Slow addition of 2-[N-(alkoxycarbonyl)amino] aldehydes to mixtures of [V 2 Cl 3 (THF) 6 ] 2 [Zn 2 Cl 6 ] and aliphatic aldehydes gave syn,syn-3-[N-(alkoxycarbonyl)amino] 1,2-diols in good yield and high enantiomeric purity (>99:1). The alkyl group of the N-alkoxycarbonyl was shown to influence the yield: Me >allyl>Bn>t-Bu. Only the syn,syn diastereomer was observed (>20:1), except with N-Cbz-alaninal

  将 2-[N-(烷氧基羰基) 氨基] 醛缓慢加入 [V 2 Cl 3 (THF) 6 ] 2 [Zn 2 Cl 6 ] 和脂肪族醛的混合物中，得到 syn,syn-3-[N-(烷氧基羰基)氨基] 1,2-二醇，收率高，对映体纯度高 (>99:1)。N-烷氧基羰基的烷基显示出影响产率：Me>烯丙基>Bn>t-Bu。除了 N-Cbz-丙氨醛 (10:1:1)、O-苄基-N-Cbz-丝氨酸 (7:1) 和 N-Cbz-脯氨酸 (5:1 到 12:1)。一种新的丝氨酸衍生物，N-Cbz-O-TBS-丝氨酸，与正十五醛交叉偶联得到木-DC 18-植物鞘氨醇的衍生物