BOC-O-苄基-L-苏氨酸N-羧酸酐 | 160803-32-7

• 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-O-苄基-L-苏氨酸N-羧酸酐
• 中文别名: BOC-O-苄基-L-苏氨酸N-羧基酸酐；N-叔丁氧羰基-O-苄基-L-苏氨酸-N-酸酐；BOC-THR(BZL)-N-羧基酸酐
• 英文名称: Boc-Thr(OBz)-NCA
• 英文别名: Boc-O-benzyl-L-threonine N-carboxy anhydride；tert-butyl (4S)-2,5-dioxo-4-[(1R)-1-phenylmethoxyethyl]-1,3-oxazolidine-3-carboxylate
• CAS: 160803-32-7
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: JKERFCFKSYDKBY-YPMHNXCESA-N

物化性质

• 熔点：
  77-80 °C
• 沸点：
  403.3±37.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  BOC-O-苄基-L-苏氨酸N-羧酸酐 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以24%的产率得到tert-butyl 3,5-bis<(R)-1-(benzyloxy)ethyl>-3-<(tert-butoxycarbonyl)amino>-2,4-dioxo-1-pyrrolodinecarboxylate
  参考文献：
  名称：

  Base-Induced Dimerization of Urethane-Protected Amino Acid N-Carboxanhydrides

  摘要：

  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.

  DOI：

  10.1021/jo951260f

文献信息

• Rapid, one-pot synthesis of urethane-protected tripeptides
  作者：Yun-Fei Zhu、William D. Fuller

  DOI：10.1016/0040-4039(94)02391-n

  日期：1995.2

  Urethane-protected tripeptides are synthesized in solution, without isolation or purification of intermediates, using urethane-protected N-carboxyanhydrides as coupling reagents and hydrogenation for removal of N-protection.

  氨基甲酸酯保护的三肽是在溶液中合成的，无需分离或纯化中间体，使用氨基甲酸酯保护的N-羧基酸酐作为偶联剂并进行氢化以去除N-保护。
• 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.