(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid

Name: (R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid
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CAS No. 204251-86-5
Cat. No. CS-0157986
Purity≥95%
MDL No.MFCD01074691

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(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid|CS-0157986

Structure of 204251-86-5

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Description

This chiral fluorenonyl-protected amino acid derivative features a bench-stable, electron-rich fluoren-9-ylmethyl carbamate group that enables efficient solid-phase peptide synthesis. The allyloxy-substituted ketone side chain provides a handle for orthogonal functionalization via olefin metathesis, while the (R)-stereochemistry ensures high fidelity in peptide coupling reactions.

Application

(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid serves as a versatile chiral building block for peptide and peptidomimetic synthesis, enabling efficient incorporation of allyl-protected hydroxyl functionalities. The fluorenylmethoxycarbonyl (Fmoc) group provides robust protection for primary amines during solid-phase synthesis, while the allyloxy substituent offers orthogonal handle for subsequent functionalization via palladium-catalyzed reactions. Bench-stable and amenable to standard purification methods, it facilitates reliable access to complex scaffolds in medicinal chemistry campaigns.

General Information

CAS No. 204251-86-5
Cat. No. CS-0157986
Purity ≥95%
MDL No. MFCD01074691
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₃H₂₃NO₆
Molecular Weight 409.43
Synonym(s) N-Fmoc-D-glutamic acid 1-allyl ester
SMILES C=CCOC([C@H](NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O)CCC(O)=O)=O

Computational Chemistry Data

TPSA 101.93
LogP 3.4877
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 9

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

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Other Classifications

Building Blocks Functional Group Olefins

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Glutamic acid and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid

CAS No. 204251-86-5

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