Description

(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-2-methyl-4-oxobutanoic acid (CAS: 1231709-26-4) is a high-purity, chiral Fmoc-protected amino acid derivative designed for advanced peptide synthesis and pharmaceutical research. With the molecular formula C₂₄H₂₇NO₆, this compound features a stereospecific (R)-configuration, an Fmoc-protected amine, and a tert-butyl ester group, ensuring compatibility with solid-phase peptide synthesis (SPPS) methodologies. Its rigid structure and orthogonal protecting groups make it ideal for constructing complex peptidomimetics and constrained peptides. Suitable for automated synthesizers, this reagent is rigorously QC-tested by HPLC and NMR to guarantee ≥95% purity, meeting the stringent demands of medicinal chemistry and bioconjugation applications. Store desiccated at -20°C for long-term stability.

Properties

• CAS Number: 1231709-26-4
• Complexity: 664
• IUPAC Name: (2R)-4-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-4-oxo-butanoic acid
• InChI: InChI=1S/C24H27NO6/c1-23(2,3)31-20(26)13-24(4,21(27)28)25-22(29)30-14-19-17-11-7-5-9-15(17)16-10-6-8-12-18(16)19/h5-12,19H,13-14H2,1-4H3,(H,25,29)(H,27,28)/t24-/m1/s1
• InChI Key: STBMKQNEFSJOCS-XMMPIXPASA-N
• Exact Mass: 425.18383758
• Molecular Formula: C24H27NO6
• Molecular Weight: 425.5
• SMILES: C[C@@](CC(=O)OC(C)(C)C)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Topological: 102
• Monoisotopic Mass: 425.18383758
• Synonyms: 1231709-26-4, (R)-Fmoc-2-amino-2-methyl-succinic acid-4-tert-butyl ester, (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-2-methyl-4-oxobutanoic acid, Fmoc-|A-Me-D-Asp(OtBu)-OH, Fmoc-alpha-Me-D-Asp(OtBu)-OH, (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid, MFCD16660844, (2R)-4-(tert-butoxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methyl-4-oxobutanoic acid, FMoc-a-Me-D-Asp(OtBu)-OH, Fmoc-beta-Me-D-Asp(OtBu)-OH, SCHEMBL18614227, DTXSID701124301, AT19321, FF72788, AS-82416, CS-0439189, (R)-N-Fmoc-alpha-Meth-ylAspartic acid -4-tert-butyl ester, (R)-Fmoc-2-Amino-2-methyl-succinic acid-4-t-butyl ester (Fmoc-alpha-Me-D-Asp(OtBu)-OH), 4-(1,1-Dimethylethyl) hydrogen N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methyl-D-aspartate, (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-2-methyl-4-oxobutanoicacid

Application

This compound serves as a key building block in the synthesis of stereochemically defined peptides, particularly in drug discovery targeting protease inhibition or GPCR modulation. Its tert-butyl ester group enables selective deprotection under mild acidic conditions, while the Fmoc group is cleaved under basic conditions, facilitating sequential peptide assembly. Applications include the development of peptide therapeutics, peptidomimetic libraries, and as a chiral auxiliary in asymmetric synthesis.

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