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Benzyl (tert-butoxycarbonyl)-L-phenylalaninate
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CAS No. 66617-58-1
- Cat. No. CS-0454717
- Purity≥98%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 66617-58-1
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General Information
- CAS No. 66617-58-1
- Cat. No. CS-0454717
- Purity ≥98%
- MDL No. None
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₂₁H₂₅NO₄
- Molecular Weight 355.43
- Synonym(s) N-tert-Butoxycarbonylphenylalanine benzyl ester
- SMILES CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)OCC2=CC=CC=C2
Description
Benzyl (tert-butoxycarbonyl)-L-phenylalaninate delivers a protected L-phenylalanine derivative with enhanced solubility and stability. The tert-butoxycarbonyl group enables efficient N-terminal protection during peptide synthesis, while the benzyl ester facilitates selective deprotection under mild conditions. This combination streamlines access to phenylalanine-containing sequences in complex synthetic workflows.
Application
Benzyl (tert-butoxycarbonyl)-L-phenylalaninate serves as a protected amino acid building block for peptide synthesis, enabling efficient N-terminal protection with orthogonal deprotection compatibility. The Boc group offers robust stability under basic conditions and facilitates mild acidic cleavage, while the benzyl ester allows selective hydrolysis. This dual protection strategy supports reliable coupling efficiency and simplifies purification in multi-step syntheses.
Synthesis
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Route1
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13734-34-4 -
In-stock
100-51-6 - ~96%
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In-stock
66617-58-1
References
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Wang, Yong; Aleiwi, Bilal A.; Wang, Qinghui; Kurosu, Michio Organic Letters, 2012 , vol. 14, # 18 p. 4910 - 4913,4 Title/Abstract Full Text Show Details Wang, Yong; Aleiwi, Bilal A.; Wang, Qinghui; Kurosu, Michio Organic Letters, 2012 , vol. 14, # 18 p. 4910 - 4913
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Route2
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13734-34-4
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100-39-0 - ~96%
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In-stock
66617-58-1
References
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UNIVERSITY OF WOLLONGONG Patent: WO2006/74501 A1, 2006 ; Location in patent: Page/Page column 79 ;
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Route3
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1155946-51-2
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13734-34-4
- ~50%
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In-stock
66617-58-1
References
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Raines, Ronald Thaddeus; Myers, Eddie Leonard Patent: US2010/125132 A1, 2010 ; Location in patent: Page/Page column 35 ;
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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 : H315-H319
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Precautionary Statements : P264-P280-P302+P352-P362
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Quality Control
Computational Chemistry Data
- TPSA 64.63
- LogP 3.8658
- H_Acceptors 4
- H_Donors 1
- Rotatable_Bonds 6
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Key Words
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