Atomfair Methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate C9H16INO4

Description Methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (CAS No. 170848-34-7) is a high-purity iodinated amino acid derivative extensively utilized in organic synthesis and pharmaceutical research. This compound, with the molecular formula C9H16INO4, serves as a versatile building block for peptide modifications and cross-coupling reactions due to its reactive iodine moiety and Boc-protected amine group. Its IUPAC name, methyl 3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate , reflects its structural precision, ensuring compatibility with sensitive synthetic protocols. Supplied as a crystalline solid, it is rigorously tested for consistency in reactivity and stability, making it ideal for nucleophilic substitutions, Suzuki-Miyaura couplings, and chiral auxiliary applications. Store under inert conditions to maintain integrity.

Description

Methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (CAS No. 170848-34-7) is a high-purity iodinated amino acid derivative extensively utilized in organic synthesis and pharmaceutical research. This compound, with the molecular formula C₉H₁₆INO₄, serves as a versatile building block for peptide modifications and cross-coupling reactions due to its reactive iodine moiety and Boc-protected amine group. Its IUPAC name, methyl 3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate, reflects its structural precision, ensuring compatibility with sensitive synthetic protocols. Supplied as a crystalline solid, it is rigorously tested for consistency in reactivity and stability, making it ideal for nucleophilic substitutions, Suzuki-Miyaura couplings, and chiral auxiliary applications. Store under inert conditions to maintain integrity.

CAS No: 170848-34-7
Molecular Formula: C9H16INO4
Molecular Weight: 329.13
Exact Mass: 329.01241
Monoisotopic Mass: 329.01241
IUPAC Name: methyl 3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
SMILES: CC(C)(C)OC(=O)NC(CI)C(=O)OC
Synonyms: Methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate, 889670-02-4, MFCD20231367, N-Boc-3-iodo-DL-alanine methyl ester, Methyl 3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

Application

Methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate is a critical intermediate in the synthesis of modified peptides and bioactive molecules, particularly in introducing iodine labels for radiopharmaceuticals. Its Boc-protected amine enables selective deprotection for further functionalization, while the iodine atom facilitates palladium-catalyzed cross-coupling reactions. Researchers also employ it in asymmetric synthesis to construct chiral centers or as a precursor for unnatural amino acids. Suitable for automated peptide synthesizers and solid-phase techniques.

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