(S)-Benzyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate

Name: (S)-Benzyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate
Brand: ChemScene
Availability: InStock
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CAS No. 13512-57-7
Cat. No. CS-0154518
Purity≥97%
MDL No.MFCD00190784

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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(S)-Benzyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate|CS-0154518

Structure of 13512-57-7

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General Information

CAS No. 13512-57-7
Cat. No. CS-0154518
Purity ≥97%
MDL No. MFCD00190784
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₂₂N₂O₅
Molecular Weight 322.36
Synonym(s) Boc-asn-obzl
SMILES CC(C)(OC(N[C@H](C(OCC1=CC=CC=C1)=O)CC(N)=O)=O)C

Description

(S)-Benzyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate is a chiral building block featuring a protected amino group and a reactive ketone, enabling selective transformations in peptide synthesis. This bench-stable derivative facilitates the construction of complex β-amino acid scaffolds under mild conditions.

Application

(S)-Benzyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate serves as a key chiral building block for the synthesis of bioactive β-lactam and peptidomimetic scaffolds. Its well-defined stereochemistry, combined with orthogonal protection of both amine and carboxyl functionalities, enables reliable downstream transformations. The molecule exhibits excellent bench stability and facilitates efficient peptide coupling, cyclization, and selective deprotection protocols in standard synthetic workflows.

Synthesis

Route1
- In-stock
  
  7536-55-2
- 100-39-0
- ~86%
- In-stock
  
  13512-57-7
References
- Bioorganic and Medicinal Chemistry, , vol. 6, # 8 p. 1185 - 1208
Route2
- 100-39-0
- ~49%
- In-stock
  
  13512-57-7
References
- WO2005/21558 A2, ; Page/Page column 214-215 ;
Route3
- In-stock
  
  7536-55-2
- ~%
- In-stock
  
  13512-57-7
References
- US6528655 B1, ;

Safety Information

Download SDS

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 107.72
LogP 1.4985
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-Benzyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate

CAS No. 13512-57-7

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