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

Name: (S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate
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CAS No. 39747-65-4
Cat. No. CS-0370464
Purity≥95%
MDL No.MFCD00190833

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(S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate|CS-0370464

Structure of 39747-65-4

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General Information

CAS No. 39747-65-4
Cat. No. CS-0370464
Purity ≥95%
MDL No. MFCD00190833
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₈N₂O₇
Molecular Weight 302.28
Synonym(s) BOC-SER-OSU
SMILES CC(C)(C)OC(N[C@@H](CO)C(ON1C(CCC1=O)=O)=O)=O

Description

This (S)-configured reagent features a pyrrolidinone-activated ester coupled with a protected amino acid side chain, enabling efficient coupling in peptide synthesis. The tert-butoxycarbonyl group provides stability and orthogonal deprotection compatibility. This scaffold facilitates selective amide bond formation under mild conditions, streamlining the assembly of complex peptide sequences.

Application

(S)-2,5-Dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate serves as a robust activated ester for the selective coupling of hydroxyl and amine functionalities. Its (S)-configured backbone enables stereocontrolled synthesis of β-hydroxy-α-amino acid derivatives, commonly used in peptide macrocyclization and peptidomimetic construction. The tert-butyl carbamate group provides orthogonal protection, while the pyrrolidinone ester moiety ensures efficient reactivity under mild conditions, facilitating purification and compatibility with sensitive substrates.

Synthesis

Route1
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- In-stock
  
  3262-72-4
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  39747-65-4
References
- Oiry; Pue; Fatome; Sentenac-Roumanou; Lion; Imbach European Journal of Medicinal Chemistry, 1992 , vol. 27, # 8 p. 809 - 817

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 122.24
LogP -0.5208
H_Acceptors 7
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Key Words

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

CAS No. 39747-65-4

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