(S)-2-((tert-Butoxycarbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid

Name: (S)-2-((tert-Butoxycarbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid
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CAS No. 394735-65-0
Cat. No. CS-0058773
Purity≥95%
MDL No.MFCD28501990

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(S)-2-((tert-Butoxycarbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid|CS-0058773

Structure of 394735-65-0

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General Information

CAS No. 394735-65-0
Cat. No. CS-0058773
Purity ≥95%
MDL No. MFCD28501990
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₁F₂NO₄
Molecular Weight 293.31
Synonym(s) tert-butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid
SMILES O=C(O)[C@@H](NC(OC(C)(C)C)=O)C1CCC(F)(F)CC1

Description

This chiral building block features a bench-stable tert-butoxycarbonyl-protected amine paired with a sterically hindered 4,4-difluorocyclohexyl moiety. The electron-deficient cyclohexane ring enhances metabolic stability, while the carboxylic acid functionality enables efficient coupling reactions in peptide synthesis and medicinal chemistry applications.

Application

(S)-2-((tert-Butoxycarbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid serves as a valuable chiral building block for the synthesis of bioactive molecules, particularly in medicinal chemistry and peptide-based drug discovery. The protected amino group enables orthogonal functionalization, while the 4,4-difluorocyclohexyl moiety imparts metabolic stability and modulates lipophilicity. Its bench-stable tert-butyl carbamate protection simplifies purification, and the molecule readily participates in standard coupling reactions, facilitating access to complex scaffolds with high stereocontrol.

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Computational Chemistry Data

TPSA 75.63
LogP 2.7898
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2-((tert-Butoxycarbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid

CAS No. 394735-65-0

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