Tert-butyl 4-benzyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate | 142955-51-9

• 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
• 英文名称: Tert-butyl 4-benzyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate
• CAS: 142955-51-9
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: MFGBEMRROYABSH-UHFFFAOYSA-N

物化性质

• 沸点：
  370.3±25.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  Tert-butyl 4-benzyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate 在 甲醇 、 4 A molecular sieve 、 水 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以41%的产率得到BOC-L-苯丙氨酸
  参考文献：
  名称：

  通过金鸡纳生物碱催化的氨基甲酸酯保护的α-氨基酸N-羧基酸酐的动力学拆分，α-氨基酸的不对称合成。

  摘要：

  DOI：

  10.1021/ja011936q
• 作为产物：
  描述：

  (+/-)-N,N-bis(tert-butoxycarbonyl)phenylalanine 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以92%的产率得到Tert-butyl 4-benzyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  N-alkoxycarbonyl amino acid N-carboxyanhydrides and N,N-dialkoxycarbonyl amino acid fluorides from N,N-diprotected amino acids

  摘要：

  用 SOCl2-DMF 活化 N,N-二叔丁氧羰基或 N-叔丁氧羰基 N-Z 氨基酸会产生受 N 保护的 N-羧基氨基酸酐，而在低温下用三聚氰酸氟化物处理则主要产生 N,N-二保护氨基酸氟化物，它们是高效的酰化剂。

  DOI：

  10.1039/c39920000812

文献信息

• 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.
• US7767811B2
  申请人：——

  公开号：US7767811B2

  公开（公告）日：2010-08-03
• Asymmetric Synthesis of α-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of Urethane-Protected α-Amino Acid <i>N</i>-Carboxyanhydrides
  作者：Jianfeng Hang、Shi-Kai Tian、Liang Tang、Li Deng

  DOI：10.1021/ja011936q

  日期：2001.12.19
• N-alkoxycarbonyl amino acid N-carboxyanhydrides and N,N-dialkoxycarbonyl amino acid fluorides from N,N-diprotected amino acids
  作者：J. Savrda、M. Wakselman

  DOI：10.1039/c39920000812

  日期：——

  Activation of N,N-bis-Boc or N-Boc N-Z amino acids with SOCl2–DMF leads to N-protected N-carboxy amino acid anhydrides, whereas treatment with cyanuric fluoride at low temperature gives mainly N,N-bis-protected amino acid fluorides, which are efficient acylating agents.

  用 SOCl2-DMF 活化 N,N-二叔丁氧羰基或 N-叔丁氧羰基 N-Z 氨基酸会产生受 N 保护的 N-羧基氨基酸酐，而在低温下用三聚氰酸氟化物处理则主要产生 N,N-二保护氨基酸氟化物，它们是高效的酰化剂。