Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate

CAS No. 93267-04-0
Cat. No. CS-M3115
Purity≥97%
MDL No.MFCD00216579

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Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate|CS-M3115

Structure of 93267-04-0

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Description

Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate features a chiral β-amino acid scaffold with a bench-stable tert-butyl carbamate protecting group and a reactive iodine handle at the γ-position. This configuration enables direct coupling in late-stage diversification, particularly in transition-metal-catalyzed cross-couplings or nucleophilic substitutions. The molecule combines synthetic versatility with predictable stereochemical integrity, streamlining access to functionalized amino acid derivatives for medicinal chemistry applications.

Application

Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate serves as a versatile chiral building block for the synthesis of β-amino acid derivatives and peptidomimetics. The iodide functionality enables palladium-catalyzed cross-coupling reactions, while the Boc-protected amine and ester groups offer orthogonal reactivity and stability under standard synthetic conditions. Its bench-stable nature and compatibility with diverse transformations make it well-suited for iterative peptide synthesis and medicinal chemistry campaigns.

General Information

CAS No. 93267-04-0
Cat. No. CS-M3115
Purity ≥97%
MDL No. MFCD00216579
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₆INO₄
Molecular Weight 329.13
Synonym(s) None
SMILES O=C(OC)[C@H](CI)NC(OC(C)(C)C)=O

Computational Chemistry Data

TPSA 64.63
LogP 1.4877
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 3

Safety Information

Download SDS

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Unnatural Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Unnatural Amino Acid Derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Biochemistry Biochemicals and Reagents Amino Acids C-ProtectedAmino Acids

Biochemistry Biochemicals and Reagents Amino Acids N-Protected Amino Acids

Key Words

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Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate

CAS No. 93267-04-0

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