(S)-1,4-Bis(tert-butoxycarbonyl)piperazine-2-carboxylic acid

Name: (S)-1,4-Bis(tert-butoxycarbonyl)piperazine-2-carboxylic acid
Brand: ChemScene
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CAS No. 788799-69-9
Cat. No. CS-M0445
Purity≥97%
MDL No.MFCD02179096

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
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(S)-1,4-Bis(tert-butoxycarbonyl)piperazine-2-carboxylic acid|CS-M0445

Structure of 788799-69-9

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General Information

CAS No. 788799-69-9
Cat. No. CS-M0445
Purity ≥97%
MDL No. MFCD02179096
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₆N₂O₆
Molecular Weight 330.38
Synonym(s) (S)-1,4-Diboc-2-Piperazine-2-Carboxylic Acid
SMILES O=C([C@H]1N(C(OC(C)(C)C)=O)CCN(C(OC(C)(C)C)=O)C1)O

Description

(S)-1,4-Bis(tert-butoxycarbonyl)piperazine-2-carboxylic acid features two robust tert-butyl carbamate protecting groups flanking a chiral piperazine core, enabling stable incorporation into complex peptide architectures. The carboxylic acid moiety provides a reactive handle for conjugation under standard coupling conditions. This configuration supports efficient synthesis of constrained peptidomimetics and cyclic scaffolds with enhanced metabolic stability.

Application

(S)-1,4-Bis(tert-butoxycarbonyl)piperazine-2-carboxylic acid serves as a versatile chiral building block for the synthesis of piperazine-based heterocycles. The molecule enables efficient construction of medicinally relevant scaffolds through orthogonal deprotection strategies, with both Boc groups offering predictable cleavage under mild acidic conditions. Its stability under ambient storage and compatibility with standard coupling protocols facilitate straightforward incorporation into peptide-like architectures and macrocyclic compounds.

Synthesis

Route1
- In-stock
  
  24424-99-5
- 147650-70-2
- ~96%
- In-stock
  
  788799-69-9
References
- Gao, Hongwu; Renslo, Adam R. Journal of Organic Chemistry, 2007 , vol. 72, # 22 p. 8591 - 8592

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 96.38
LogP 1.9274
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Piperazine compounds

Key Words

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(S)-1,4-Bis(tert-butoxycarbonyl)piperazine-2-carboxylic acid

CAS No. 788799-69-9

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