(S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

Name: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid
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CAS No. 138775-03-8
Cat. No. CS-0127816
Purity≥98%
MDL No.MFCD02179111

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(S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid|CS-0127816

Structure of 138775-03-8

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General Information

CAS No. 138775-03-8
Cat. No. CS-0127816
Purity ≥98%
MDL No. MFCD02179111
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₄N₂O₆
Molecular Weight 364.39
Synonym(s) (S)-N-1-Boc-N-4-Cbz-2-piperazinecarboxylic acid
SMILES O=C([C@H]1N(C(OC(C)(C)C)=O)CCN(C(OCC2=CC=CC=C2)=O)C1)O

Description

This chiral piperazine derivative features a (S)-configured backbone with orthogonal protecting groups: a benzyloxycarbonyl at the 4-position and a tert-butoxycarbonyl at the 1-position, enabling selective deprotection during peptide coupling. The carboxylic acid at the 2-position facilitates conjugation in synthetic sequences. Designed for modular assembly of bioactive scaffolds, this compound exhibits excellent stability under standard bench conditions and compatibility with diverse reaction environments.

Application

(S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid serves as a versatile chiral building block for the synthesis of piperazine-based pharmaceutical intermediates. The protected piperazine core enables orthogonal functionalization, with the benzyloxycarbonyl and tert-butoxycarbonyl groups offering stable, orthogonal protection for amine and carboxylic acid functionalities. Its bench-stable nature and compatibility with standard coupling reactions facilitate efficient access to complex heterocyclic scaffolds in medicinal chemistry campaigns.

Synthesis

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- 194934-75-3
- ~%
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  138775-03-8
References
- Journal of the American Chemical Society, , vol. 123, # 30 p. 7207 - 7219
Route2
- In-stock
  
  98541-64-1
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References
- Journal of Organic Chemistry, , vol. 62, # 18 p. 6439 - 6440
Route3
- 501-53-1
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- In-stock
  
  138775-03-8
References
- Journal of Organic Chemistry, , vol. 62, # 18 p. 6439 - 6440

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 96.38
LogP 2.3291
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Piperazine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

138775-03-8 sigma138775-03-8 manufacturer138775-03-8 price138775-03-8 structure138775-03-8 SDSbuy 138775-03-8138775-03-8 supplier138775-03-8 uses138775-03-8 molecular weightprice of 138775-03-8138775-03-8 chemical name formula of 138775-03-8

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(S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

CAS No. 138775-03-8

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