(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

Name: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid
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CAS No. 244132-27-2
Cat. No. CS-W021150
Molecule weight452.50
Purity≥95%
MDL No.MFCD01860733

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(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid|CS-W021150

Structure of 244132-27-2

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General Information

CAS No. 244132-27-2
Cat. No. CS-W021150
Purity ≥95%
MDL No. MFCD01860733
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₅H₂₈N₂O₆
Molecular Weight 452.50
Synonym(s) FMOC-(2S)-PIPERAZINYL(4-N-BOC)
SMILES O=C([C@H]1N(C(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O)CCN(C(OC(C)(C)C)=O)C1)O

Description

This (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid features a chiral piperazine core with orthogonal protecting groups: the fluorenylmethoxycarbonyl (Fmoc) at nitrogen and tert-butoxycarbonyl (Boc) at the C4 position, enabling selective deprotection in peptide synthesis. The Fmoc group ensures stable storage and efficient removal under mild basic conditions, while the Boc moiety provides robust protection during acidic processing steps. This combination facilitates precise, stepwise assembly of complex peptide architectures without side reactions.

Application

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid serves as a robust, bench-stable dipeptide building block for the synthesis of complex peptidomimetics and macrocyclic scaffolds. Its orthogonal protection—fluorenylmethoxycarbonyl (Fmoc) at the primary amine and tert-butyl carbamate at the secondary amine—enables selective deprotection in solid-phase peptide synthesis. The piperazine core facilitates diverse functionalization and serves as a key structural motif in bioactive molecules, offering enhanced solubility and conformational rigidity.

Synthesis

Route1
- 28920-43-6
- In-stock
  
  848482-93-9
- ~44%
- In-stock
  
  244132-27-2
References
- Blizzard, Timothy A.; Singh, Sanjay; Patil, Basanagoud; Chidurala, Naresh; Komanduri, Venukrishnan; Debnath, Samarpita; Belyakov, Sergei; Crespo, Alejandro; Struck, Alice; Kurtz, Marc; Wiltsie, Judyann; Shen, Xun; Sonatore, Lisa; Arocho, Marta; Lewis, Dale; Ogletree, Martin; Biftu, Tesfaye Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 4 p. 1111 - 1115

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

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Computational Chemistry Data

TPSA 96.38
LogP 3.9414
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aliphatic heterocycle compounds Piperazine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

CAS No. 244132-27-2

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