(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(allyloxy)-4-oxobutanoic acid

Name: (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(allyloxy)-4-oxobutanoic acid
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CAS No. 177609-12-0
Cat. No. CS-0067980
Molecule weight395.41
Purity≥97%
MDL No.MFCD01074688

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(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(allyloxy)-4-oxobutanoic acid|CS-0067980

Structure of 177609-12-0

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General Information

CAS No. 177609-12-0
Cat. No. CS-0067980
Purity ≥97%
MDL No. MFCD01074688
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₂H₂₁NO₆
Molecular Weight 395.41
Synonym(s) N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-D-ASPARTIC ACID BETA ALLYL ESTER
SMILES O=C(OCC=C)C[C@H](C(O)=O)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(allyloxy)-4-oxobutanoic acid features a fluorenylmethyl carbamate (Fmoc) protecting group for amine-directed synthesis, combined with a reactive allyloxy-ketone moiety enabling orthogonal functionalization. This bifunctional architecture supports efficient incorporation into peptide and peptidomimetic scaffolds under standard coupling conditions.

Application

(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(allyloxy)-4-oxobutanoic acid serves as a versatile chiral building block for peptide and peptidomimetic synthesis, enabling efficient incorporation of allyl-containing side chains. The fluorenylmethoxycarbonyl (Fmoc) group provides robust protection with convenient removal under mild basic conditions, while the allyloxy ketone moiety offers orthogonal functionality for subsequent transformations. This compound exhibits excellent bench stability, facilitates straightforward purification, and functions effectively in solid-phase and solution-phase workflows.

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 101.93
LogP 3.0976
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 8

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Aspartic acid and derivatives

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)-4-(allyloxy)-4-oxobutanoic acid

CAS No. 177609-12-0

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