(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)-2-methylpropanoic acid

Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)-2-methylpropanoic acid
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CAS No. 914399-98-7
Cat. No. CS-0119797
Purity≥98%
MDL No.MFCD26793609

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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)-2-methylpropanoic acid|CS-0119797

Structure of 914399-98-7

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General Information

CAS No. 914399-98-7
Cat. No. CS-0119797
Purity ≥98%
MDL No. MFCD26793609
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₃H₂₇NO₅
Molecular Weight 397.46
Synonym(s) FMoc-α-Me-Ser(tBu)-OH
SMILES O=C(O)[C@@](COC(C)(C)C)(C)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)-2-methylpropanoic acid is a sterically hindered, bench-stable amino acid derivative featuring a fluorenylmethoxycarbonyl (Fmoc) protecting group and a tert-butoxy-substituted side chain. This configuration enhances solubility in organic solvents and improves coupling efficiency during solid-phase peptide synthesis. The chiral center at the alpha position ensures enantiomeric purity essential for sequence-specific assembly of biologically active peptides.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)-2-methylpropanoic acid serves as a robust, bench-stable chiral building block for peptide synthesis and heterocyclic scaffold construction. Its tert-butyl ester functionality enables selective deprotection under mild acidic conditions, while the Fmoc group ensures orthogonal protection during multi-step sequences. The sterically hindered α-methyl-α-alkoxy motif enhances diastereoselectivity in coupling reactions and facilitates purification via standard chromatographic methods.

Safety Information

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Computational Chemistry Data

TPSA 84.86
LogP 4.1835
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Serine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)-2-methylpropanoic acid

CAS No. 914399-98-7

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