(S)-2-(((Benzyloxy)carbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid

Name: (S)-2-(((Benzyloxy)carbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid
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CAS No. 1266228-88-9
Cat. No. CS-0255782
Purity≥98%
MDL No.None

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(S)-2-(((Benzyloxy)carbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid|CS-0255782

Structure of 1266228-88-9

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General Information

CAS No. 1266228-88-9
Cat. No. CS-0255782
Purity ≥98%
MDL No. None
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₁₉F₂NO₄
Molecular Weight 327.32
Synonym(s) None
SMILES O=C(OCC1=CC=CC=C1)N[C@@H](C2CCC(F)(CC2)F)C(O)=O

Description

(S)-2-(((Benzyloxy)carbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid features a sterically hindered cyclohexyl core with dual fluorine atoms enhancing metabolic stability. The benzyloxycarbonyl (Boc) group provides orthogonal protection for the amine, enabling selective deprotection during peptide synthesis. This chiral building block integrates efficiently into complex molecular architectures requiring precise stereocontrol and robust functional group tolerance under standard bench conditions.

Application

(S)-2-(((Benzyloxy)carbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid serves as a versatile chiral building block for the synthesis of bioactive molecules, particularly in peptide and medicinal chemistry. The benzyloxycarbonyl (Cbz) group provides stable protection of the amine, enabling selective deprotection under mild hydrogenolysis conditions. The 4,4-difluorocyclohexyl moiety imparts enhanced metabolic stability and modulates lipophilicity, making this scaffold valuable for optimizing drug-like properties in targeted compound libraries.

Safety Information

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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

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Computational Chemistry Data

TPSA 75.63
LogP 3.1915
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 5

Other Classifications

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2-(((Benzyloxy)carbonyl)amino)-2-(4,4-difluorocyclohexyl)acetic acid

CAS No. 1266228-88-9

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