4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)tetrahydro-2H-pyran-4-carboxylic acid

Name: 4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)tetrahydro-2H-pyran-4-carboxylic acid
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CAS No. 285996-72-7
Cat. No. CS-0101125
Purity≥97%
MDL No.MFCD02683137

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4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)tetrahydro-2H-pyran-4-carboxylic acid|CS-0101125

Structure of 285996-72-7

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General Information

CAS No. 285996-72-7
Cat. No. CS-0101125
Purity ≥97%
MDL No. MFCD02683137
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₂₁NO₅
Molecular Weight None
Synonym(s) 4-(FMOC-AMINO)-TETRAHYDROPYRAN-4-CARBOXYLIC ACID
SMILES O=C(C1(NC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O)CCOCC1)O

Description

This fluorenylmethoxycarbonyl-protected tetrahydropyran carboxylic acid serves as a specialized amino acid surrogate in peptide synthesis. The C-terminal carbamate functionality enables orthogonal deprotection, while the fluoren-9-ylmethoxy carbonyl group ensures high coupling efficiency and minimal side reactions under standard conditions.

Application

4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)tetrahydro-2H-pyran-4-carboxylic acid serves as a versatile protected amino acid building block, enabling efficient peptide coupling and heterocyclic scaffold construction. The Fmoc group provides excellent stability under basic conditions and facilitates straightforward deprotection, while the tetrahydropyran-4-carboxylic acid moiety offers a rigid, hydrophobic core suitable for medicinal chemistry applications. Its compatibility with standard solid-phase synthesis protocols and ease of purification make it a practical choice for complex molecule assembly.

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Computational Chemistry Data

TPSA 84.86
LogP 3.1589
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Fmoc

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)tetrahydro-2H-pyran-4-carboxylic acid

CAS No. 285996-72-7

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