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

Name: (1S,2R)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 137170-89-9
Cat. No. CS-0037061
Purity≥96%
MDL No.MFCD09750528

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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(1S,2R)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid|CS-0037061

Structure of 137170-89-9

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General Information

CAS No. 137170-89-9
Cat. No. CS-0037061
Purity ≥96%
MDL No. MFCD09750528
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₉NO₄
Molecular Weight 229.27
Synonym(s) (1S,2R)-2-(Boc-amino)cyclopentanecarboxylic Acid
SMILES OC([C@@H]1[C@H](NC(OC(C)(C)C)=O)CCC1)=O

Description

This chiral cyclopentane derivative features a protected amino group and a carboxylic acid handle, enabling direct incorporation into peptide syntheses. The (1S,2R) stereochemistry ensures high diastereoselectivity in coupling reactions, while the tert-butoxycarbonyl group provides robust protection under standard conditions.

Application

(1S,2R)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid serves as a stereochemically defined building block for cyclopentane-based peptidomimetics and bioactive heterocycles. The Boc-protected amine and carboxylic acid functionalities enable orthogonal derivatization in solid-phase synthesis, while the rigid cyclopentane scaffold imparts conformational stability. Bench-stable and readily purified by chromatography, it facilitates efficient access to diverse cyclic peptide analogs and pharmaceutical intermediates.

Synthesis

Route1
- In-stock
  
  24424-99-5
- 64191-14-6
- ~75%
- In-stock
  
  137170-89-9
References
- BRISTOL-MYERS SQUIBB COMPANY Patent: WO2009/15166 A1, 2009 ; Location in patent: Page/Page column 76-77 ; WO 2009/015166 A1
Route2
- In-stock
  
  136315-70-3
- ~%
- In-stock
  
  137170-89-9
References
- Tetrahedron, , vol. 53, # 23 p. 7975 - 7984

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 Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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

CAS No. 137170-89-9

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