(1R,2R)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

Name: (1R,2R)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 245115-25-7
Cat. No. CS-0356790
Purity≥97%
MDL No.MFCD04974223

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(1R,2R)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid|CS-0356790

Structure of 245115-25-7

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General Information

CAS No. 245115-25-7
Cat. No. CS-0356790
Purity ≥97%
MDL No. MFCD04974223
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₉NO₄
Molecular Weight 229.27
Synonym(s) (1R,2R)-Boc-Acpc
SMILES O=C([C@H]1[C@H](NC(OC(C)(C)C)=O)CCC1)O

Description

This chiral cyclopentane-based amino acid derivative features a protected amine and carboxylic acid group, enabling direct incorporation into peptide synthesis workflows. The (1R,2R) stereochemistry ensures high diastereoselectivity in cyclization reactions, while the tert-butoxycarbonyl (Boc) group provides stability under standard conditions and facilitates selective deprotection.

Application

(1R,2R)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid serves as a stereochemically defined building block for cyclopentane-based peptidomimetics and bioactive scaffolds. The Boc-protected amine enables straightforward deprotection and coupling in solid-phase and solution-phase synthesis. Its rigid cyclopentane core provides conformational constraint, enhancing target selectivity in medicinal chemistry applications. The carboxylic acid functionality facilitates direct amidation or esterification, supporting versatile downstream derivatization. Bench-stable and easily purified by standard chromatographic methods, it functions reliably in multi-step synthetic sequences.

Synthesis

Route1
- 245115-20-2
- ~66%
- In-stock
  
  245115-25-7
References
- Appella, Daniel H.; Christianson, Laurie A.; Klein, Daniel A.; Richards, Michele R.; Powell, Douglas R.; Gellman, Samuel H. Journal of the American Chemical Society, 1999 , vol. 121, # 33 p. 7574 - 7581
Route2
- In-stock
  
  611-10-9
- ~%
- In-stock
  
  245115-25-7
References
- Journal of the American Chemical Society, , vol. 126, # 46 p. 15067 - 15073
Route3
- 163877-11-0
- ~%
- In-stock
  
  245115-25-7
References
- Journal of the American Chemical Society, , vol. 126, # 46 p. 15067 - 15073

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 75.63
LogP 1.7644
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Fatty ring compounds Cyclopentane compounds

Key Words

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(1R,2R)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

CAS No. 245115-25-7

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