Lot numbers can be found on the outside label of a product:
Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate
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CAS No. 93267-04-0
- Cat. No. CS-M3115
- Purity≥97%
- MDL No.MFCD00216579
*For research and further manufacturing use only, not for direct human use.
Structure of 93267-04-0
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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
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.
Synthesis
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Route1
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In-stock
2766-43-0 - ~87%
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In-stock
93267-04-0
References
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Crich, David; Rahaman, Md. Yeajur Journal of Organic Chemistry, 2009 , vol. 74, # 17 p. 6792 - 6796
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Route2
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In-stock
56926-94-4 - ~83%
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In-stock
93267-04-0
References
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Stocking, Emily M.; Schwarz, Jessie N.; Senn, Hans; Salzmann, Michael; Silks, Louis A. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 16 p. 2443 - 2447
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Route3
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187035-34-3 - ~%
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In-stock
93267-04-0
References
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Synlett, , vol. 1997, # 2 p. 169 - 170
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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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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Quality Control
Computational Chemistry Data
- TPSA 64.63
- LogP 1.4877
- H_Acceptors 4
- H_Donors 1
- Rotatable_Bonds 3
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Other Classifications
- 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
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Key Words
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