(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)hex-5-enoic acid

Name: (R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)hex-5-enoic acid
Brand: ChemScene
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CAS No. 269726-95-6
Cat. No. CS-0158036
Purity≥97%
MDL No.None

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(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)hex-5-enoic acid|CS-0158036

Structure of 269726-95-6

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General Information

CAS No. 269726-95-6
Cat. No. CS-0158036
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₂₁NO₄
Molecular Weight 351.40
Synonym(s) Fmoc-(R)-3-Amino-5-hexenoic acid
SMILES C=CC[C@@H](NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O)CC(O)=O

Description

(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)hex-5-enoic acid features a chiral α-amino acid backbone with a pendant enoate handle, enabling efficient conjugation in peptide synthesis. The fluorenylmethoxycarbonyl (Fmoc) group provides orthogonal protection, while the terminal alkene supports post-functionalization via click chemistry or polymer coupling. Bench-stable and moisture-tolerant, this derivative streamlines the incorporation of functionalized amino acids into complex biomolecules under standard conditions.

Application

(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)hex-5-enoic acid serves as a valuable chiral building block for peptide synthesis and medicinal chemistry applications. The fluorenylmethoxycarbonyl (Fmoc) group enables efficient, orthogonal protection of primary amines under mild conditions, while the terminal alkene facilitates downstream functionalization via standard olefin transformations. Bench-stable and readily purified by flash chromatography, it supports robust coupling protocols in solid-phase and solution-phase syntheses.

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

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Computational Chemistry Data

TPSA 75.63
LogP 3.9445
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 7

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Olefins

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)hex-5-enoic acid

CAS No. 269726-95-6

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