(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid

Name: (R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid
Brand: ChemScene
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CAS No. 156881-63-9
Cat. No. CS-0154584
Molecule weight243.30
Purity≥97%
MDL No.MFCD00671402

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Type	HazMat Fee
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(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid|CS-0154584

Structure of 156881-63-9

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General Information

CAS No. 156881-63-9
Cat. No. CS-0154584
Purity ≥97%
MDL No. MFCD00671402
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₂₁NO₄
Molecular Weight 243.30
Synonym(s) N-tert-Butoxycarbonyl-D-Cyclopentylglycine
SMILES CC(C)(OC(N[C@@H](C(O)=O)C1CCCC1)=O)C

Description

(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid is a chiral building block featuring a sterically encumbered cyclopentyl group and a bench-stable Boc-protected amine. This configuration enables selective incorporation into peptidomimetics and bioactive scaffolds, where the rigid cyclopentyl moiety imparts conformational constraint. The Boc group facilitates straightforward deprotection under mild acidic conditions, streamlining downstream functionalization in synthetic sequences.

Application

(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid serves as a versatile chiral building block for the synthesis of cyclopentyl-containing peptides and bioactive molecules. The Boc-protected amine enables straightforward deprotection under mild acidic conditions, while the pendant cyclopentyl group provides conformational rigidity beneficial for structure-activity studies. Its bench-stable nature and compatibility with standard coupling protocols facilitate efficient peptide elongation and modular scaffold construction in medicinal chemistry workflows.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  2521-86-0
- ~81%
- In-stock
  
  156881-63-9
References
- Goodfellow, Val S.; Marathe, Manoj V.; Kuhlman, Karen G.; Fitzpatrick, Timothy D.; Cuadrado, David; Hanson, Wendy; Zuzack, John S.; Ross, Sherman E.; Wieczorek, Maciej; Burkard, Michael; Whalley, Eric T. Journal of Medicinal Chemistry, 1996 , vol. 39, # 7 p. 1472 - 1484
Route2
- 188347-99-1
- ~%
- In-stock
  
  156881-63-9
References
- Tetrahedron, , vol. 53, # 4 p. 1275 - 1294

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P264-P302+P352-P304+P340

Quality Control

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Computational Chemistry Data

TPSA 75.63
LogP 2.1545
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Glycine and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid

CAS No. 156881-63-9

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