BOC-异亮氨酸-琥珀酰胺 | 145929-76-6

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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
• 中文名称: BOC-异亮氨酸-琥珀酰胺
• 英文名称: N-(tert-butoxycarbonyl)-L-isoleucine N-carboxyanhydride
• 英文别名: Boc-L-Ile-NCA；(S)-tert-Butyl 4-((S)-sec-butyl)-2,5-dioxooxazolidine-3-carboxylate；tert-butyl (4S)-4-[(2S)-butan-2-yl]-2,5-dioxo-1,3-oxazolidine-3-carboxylate
• CAS: 145929-76-6
• 化学式: C₁₂H₁₉NO₅
• 分子量: 257.287
• InChiKey: LXDDJFOBMDAQJT-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  BOC-异亮氨酸-琥珀酰胺 在 lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到2-甲基-2-丙基[(2S,3S)-3-甲基-1-氧代-2-戊烷基]氨基甲酸酯
  参考文献：
  名称：

  通过还原N-保护的N-羧基酸酐（UNCA）合成手性N-保护的α-氨基醛

  摘要：

  描述了在温和条件下容易地一步合成多种N-保护的（Boc，Z，Fmoc）α-氨基醛的方法。通过用等量的三（叔丁氧基）锂铝还原N-保护的（Z，Boc，Fmoc）-N-羧基酸酐（UNCA），可以高收率获得纯N-保护的（Boc，Z，Fmoc）α-氨基醛。氢化物[LiAlH（Ot-Bu）3 ]或氢化三[（3-乙基-3-戊基）氧基]氢化铝锂（LTEPA）作为溶剂。该反应简单，快速并且进行时没有可检测的外消旋作用。

  DOI：

  10.1016/0040-4039(94)88419-6

文献信息

• Synthesis of N-protected γ-amino-β-keto-esters from urethane N-carboxyanhydrides (UNCAs)
  作者：Marielle Paris、Jean-Alain Fehrentz、Annie Heitz、Albert Loffet、Jean Martinez

  DOI：10.1016/0040-4039(96)01973-9

  日期：1996.11

  N-protected γ-amino-β-keto-esters were synthesized from the corresponding N-protected N-carboxyanhydride (UNCAs) by reaction with the lithium enolate of ethyl acetate in good yields. These compounds are precursors of statine derivatives.

  通过与乙酸乙酯的烯醇锂反应，由相应的N-保护的N-羧基酸酐（UNCA）合成N-保护的γ-氨基-β-酮酸酯。这些化合物是他汀类衍生物的前体。
• Synthesis of N-urethane protected α-alkyl-γ-amino-β-keto-esters from urethane N-carboxyanhydrides (UNCAs)
  作者：Marielle Paris、Jean-Alain Fehrentz、Annie Heitz、Jean Martinez

  DOI：10.1016/s0040-4039(98)00026-4

  日期：1998.3

  N-protected α-alkyl-γ-amino-β-keto-esters were synthesized from the corresponding N-urethane protected N-carboxyanhydride (UNCAs) by reaction with lithium enolates in fairly good yields. These compounds are candidates for mimicking the transition state analogue in enzyme inhibitors. They constitute, however, interesting and diverse building blocks for using in combinatorial chemistry.

  N-保护的α-烷基-γ-氨基-β-酮酸酯是由相应的N-氨基甲酸酯保护的N-羧基酸酐（UNCA）通过与烯醇锂反应合成的，收率很高。这些化合物是模拟酶抑制剂中过渡态类似物的候选物。但是，它们构成了用于组合化学的有趣且多样化的构建基块。
• Lerchen, Hans-Georg; Von Dem Bruch, Karsten, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 8, p. 753 - 760
  作者：Lerchen, Hans-Georg、Von Dem Bruch, Karsten

  DOI：——

  日期：——
• Base-Induced Dimerization of Urethane-Protected Amino Acid <i>N</i>-Carboxanhydrides
  作者：Johann J. Leban、Kimberly L. Colson

  DOI：10.1021/jo951260f

  日期：1996.1.1

  tert-Butyloxycarbonyl-protected N-carboxanhydrides of amino acids dimerize in the presence of base in aprotic media to form 3,5-dialkyl-2,4-dioxo-1-pyrrolidine analogs. Depending on the nature of the base, different ratios of isomers were obtained. The reaction with lithium bis(trimethylsilyl)amide lead to one isomer only. After deprotection of the tert-butyloxycarbonyl groups and coupling of (benzyloxycarbonyl)valine, a homogeneous product was obtained. Reduction with sodium borohydride again gave a homogeneous product. Nuclear Overhauser enhancement spectroscopy and X-ray crystallography identified the stereochemistry in positions 3 and 5 of the pyrolidine as Z. When 1, 8-diazabicyclo[5.4.0]undec-7-ene was used as the base, the condensation led to a 1:3 ratio of isomers. The major isomer was different from the one obtained with lithium bis(trimethylsilyl)amide. The (benzyloxycarbonyl)valine derivative from this compound was obtained as a 1:1 mixture of isomers, leading to the conclusion that this condensation product was an enantiomeric mixture of the E isomers. The pure Z isomer from the lithium bis(trimethylsilyl)amide reaction was converted to a mixture of Z and E isomers in a ratio of 1:3 when, treated with 1,8-diazabizycol[5.4.0]undec-7-ene. The (benzyloxycarbonyl)valine derivative of the E isomer from this conversion was again a 1:1 mixture; therefore, the Z isomer obtained with lithium bis(trimethylsilyl)amide was believed to have been an enantiomeric mixture. Several other examples indicated that this reaction occurred also with other tert-butyloxycarbonyl-protected N-carboxy-anhydrides.