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

Name: Benzyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate
Brand: ChemScene
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CAS No. 108957-20-6
Cat. No. CS-0138067
Molecule weight405.23
Purity≥97%
MDL No.MFCD00191868

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Benzyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate|CS-0138067

Structure of 108957-20-6

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General Information

CAS No. 108957-20-6
Cat. No. CS-0138067
Purity ≥97%
MDL No. MFCD00191868
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₀INO₄
Molecular Weight 405.23
Synonym(s) N-Boc-3-Iodo-L-alanine benzyl ester
SMILES O=C([C@H](CI)NC(OC(C)(C)C)=O)OCC1=CC=CC=C1

Description

Benzyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate is a chiral building block featuring a stereodefined (R)-configuration at the alpha carbon. The tert-butoxycarbonyl group provides stable protection of the amine, while the iodide enables subsequent cross-coupling reactions. This bench-stable reagent integrates efficiently into peptide and heterocyclic synthesis workflows.

Application

Benzyl (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 benzyl ester groups offer orthogonal handling and stability under standard synthetic conditions. This compound facilitates efficient access to complex scaffolds in medicinal chemistry workflows.

Synthesis

Route1
- In-stock
  
  59524-02-6
- ~87%
- In-stock
  
  108957-20-6
References
- Koseki, Yohei; Yamada, Haruka; Usuki, Toyonobu Tetrahedron Asymmetry, 2011 , vol. 22, # 5 p. 580 - 586
Route2
- 94882-74-3
- ~79%
- In-stock
  
  108957-20-6
References
- 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
Route3
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  108957-20-6
References
- Journal of the Chemical Society - Perkin Transactions 1, , # 16 p. 2443 - 2447

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P233-P260-P261-P264-P271-P280-P302+P352-P304+P340-P340-P362-P403-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 64.63
LogP 3.0581
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Iodide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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

CAS No. 108957-20-6

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