(S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

Name: (S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate
Brand: ChemScene
Availability: InStock
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CAS No. 3674-06-4
Cat. No. CS-W009784
Purity≥96%
MDL No.MFCD00037911

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(S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate|CS-W009784

Structure of 3674-06-4

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General Information

CAS No. 3674-06-4
Cat. No. CS-W009784
Purity ≥96%
MDL No. MFCD00037911
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₂N₂O₆
Molecular Weight 362.38
Synonym(s) Boc-Phe-OSu
SMILES O=C(ON1C(CCC1=O)=O)[C@H](CC2=CC=CC=C2)NC(OC(C)(C)C)=O

Description

(S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate features a chiral pyrrolidinone ester scaffold paired with a protected phenylalanine-derived amine. This bench-stable acylating agent enables efficient peptide coupling under mild conditions, offering high reactivity and minimal racemization during synthetic workflows.

Application

(S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate serves as a robust activated ester for peptide synthesis, enabling efficient amide bond formation under mild conditions. The (S)-configured β-phenylalanine derivative features excellent bench stability and compatibility with diverse functional groups, facilitating straightforward purification via flash chromatography. Its tert-butyl carbamate protecting group allows orthogonal deprotection in multistep syntheses, making it ideal for constructing complex peptide scaffolds and bioactive heterocycles.

Synthesis

Route1
- In-stock
  
  6066-82-6
- 13734-34-4
- ~98%
- In-stock
  
  3674-06-4
References
- Lyubeznova, M. R.; Karpeiskaya, E. I.; Klabunovskii, E. I. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990 , vol. 39, # 4.1 p. 720 - 726 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990 , # 4 p. 811 - 818
Route2
- 13734-34-4
- 96935-01-2
- ~98%
- In-stock
  
  3674-06-4
References
- Howard, Nigel I.; Bugg, Timothy D. H. Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 14 p. 3083 - 3099
Route3
- 13734-34-4
- 90704-86-2
- ~92%
- In-stock
  
  3674-06-4
References
- Il'ina, A. V.; Davidovich, Yu. A.; Rogozhin, S. V.; Moiseenkov, A. M. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1984 , vol. 33, p. 1067 - 1070 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1984 , # 5 p. 1163 - 1165

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 102.01
LogP 1.7296
H_Acceptors 6
H_Donors 1
Rotatable_Bonds 5

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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(S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

CAS No. 3674-06-4

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