Description

N-Boc-3-Iodo-L-alanine benzyl ester (CAS No. 108957-20-6) is a high-purity, synthetic amino acid derivative designed for advanced research and pharmaceutical applications. This compound, with the molecular formula C₁₅H₂₀INO₄, is a protected form of L-alanine featuring a Boc (tert-butoxycarbonyl) group and a benzyl ester moiety, making it an essential intermediate in peptide synthesis and medicinal chemistry. Its IUPAC name, benzyl (2R)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate, reflects its stereospecific (R)-configuration, ensuring optimal compatibility with chiral synthesis protocols. Ideal for researchers, this product is rigorously tested for purity and stability, supplied in sealed packaging to maintain integrity. Store under inert conditions at recommended temperatures to preserve reactivity.

Properties

• CAS Number: 108957-20-6
• Complexity: 348
• IUPAC Name: benzyl (2R)-2-(tert-butoxycarbonylamino)-3-iodo-propanoate
• InChI: InChI=1S/C15H20INO4/c1-15(2,3)21-14(19)17-12(9-16)13(18)20-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,19)/t12-/m0/s1
• InChI Key: DDXFSYLOWHQCEK-LBPRGKRZSA-N
• Exact Mass: 405.04371
• Molecular Formula: C15H20INO4
• Molecular Weight: 405.23
• SMILES: CC(C)(C)OC(=O)N[C@@H](CI)C(=O)OCC1=CC=CC=C1
• Topological: 64.6
• Monoisotopic Mass: 405.04371
• Synonyms: 108957-20-6, N-Boc-3-Iodo-L-alanine benzyl ester, DTXSID00373549, DTXCID50324581, (R)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate, Boc-|A-iodo-Ala-OBzl, Boc-beta-iodo-Ala-OBzl, MFCD00191868, benzyl (2R)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate, (R)-benzyl 2-(tert-butoxycarbonylamino)-3-iodopropanoate, benzyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-iodopropanoate, Boc- beta -iodo-Ala-OBzl, SCHEMBL1731144, Boc-beta-iodo-Ala-OBzl, 97%, DDXFSYLOWHQCEK-LBPRGKRZSA-N, (r)-2-tert-butoxycarbonylamino-3-iodo-propionic acid benzyl ester, Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3-iodo-, phenylmethyl ester, AKOS016842397, AC-6552, AS-38532, FB155075, CS-0138067, (R)-Benzyl2-((tert-butoxycarbonyl)amino)-3-iodopropanoate, Benzyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate, (R)-2-t-butoxycarbonylamino-3-iodo-propionic acid benzyl ester

Application

N-Boc-3-Iodo-L-alanine benzyl ester is widely used in peptide synthesis as a key building block for introducing iodinated alanine residues into peptide chains. Its Boc-protected amine group allows selective deprotection under mild acidic conditions, enabling sequential coupling in solid-phase peptide synthesis (SPPS). The benzyl ester moiety facilitates further modifications or deprotection under hydrogenolysis. This compound is particularly valuable in radiopharmaceutical research for incorporating iodine isotopes (¹²³I, ¹²⁵I) into bioactive peptides. It also serves as a precursor for synthesizing unnatural amino acids and enzyme inhibitors.

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