(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((allyloxy)carbonyl)amino)propanoic acid

Name: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((allyloxy)carbonyl)amino)propanoic acid
Brand: ChemScene
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CAS No. 178924-05-5
Cat. No. CS-0100964
Purity≥98%
MDL No.MFCD01076137

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(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((allyloxy)carbonyl)amino)propanoic acid|CS-0100964

Structure of 178924-05-5

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General Information

CAS No. 178924-05-5
Cat. No. CS-0100964
Purity ≥98%
MDL No. MFCD01076137
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₂H₂₂N₂O₆
Molecular Weight 410.42
Synonym(s) N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-BETA-ALLYLOXYCARBONYL-D-2,3-DIAMINOPROPIONIC ACID
SMILES O=C(O)[C@@H](CNC(OCC=C)=O)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((allyloxy)carbonyl)amino)propanoic acid features a chiral backbone with orthogonal protecting groups: the fluorenylmethyl (Fmoc) moiety enables reliable N-terminal protection in peptide synthesis, while the allyloxycarbonyl group offers orthogonal deprotection under mild conditions. This combination facilitates sequential coupling and selective removal during complex peptide assembly. The molecule exhibits excellent solubility in common organic solvents and stability under standard bench conditions, simplifying handling and integration into automated workflows.

Application

(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((allyloxy)carbonyl)amino)propanoic acid serves as a robust chiral building block for peptide synthesis, enabling efficient incorporation of protected amino acids via standard coupling protocols. The Fmoc group ensures orthogonal deprotection under mild basic conditions, while the allyloxycarbonyl moiety provides complementary stability and selective removal via palladium-catalyzed cleavage. Its bench-stable nature and compatibility with diverse reaction conditions facilitate streamlined synthetic workflows in medicinal chemistry and peptide library development.

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 113.96
LogP 2.8905
H_Acceptors 5
H_Donors 3
Rotatable_Bonds 8

Other Classifications

Building Blocks Functional Group Fmoc

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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(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((allyloxy)carbonyl)amino)propanoic acid

CAS No. 178924-05-5

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