Lot numbers can be found on the outside label of a product:
(S)-3-Benzyloxycarbonylamino-2-(Boc-amino)propionic acid
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CAS No. 65710-57-8
- Cat. No. CS-W003499
- Purity≥95%
- MDL No.MFCD08275856
*For research and further manufacturing use only, not for direct human use.
Structure of 65710-57-8
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General Information
- CAS No. 65710-57-8
- Cat. No. CS-W003499
- Purity ≥95%
- MDL No. MFCD08275856
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₆H₂₂N₂O₆
- Molecular Weight 338.36
- Synonym(s) None
- SMILES O=C(O)[C@H](CNC(OCC1=CC=CC=C1)=O)NC(OC(C)(C)C)=O
Description
(S)-3-Benzyloxycarbonylamino-2-(Boc-amino)propionic acid features a chiral backbone with orthogonal protecting groups: a benzyl ester at the C-terminal carboxylate and a tert-butoxycarbonyl group on the side-chain amine. This dual protection enables selective deprotection during peptide synthesis, streamlining access to functionalized amino acid intermediates. The molecule exhibits excellent stability under standard bench conditions and facilitates efficient coupling reactions in solid-phase and solution-phase workflows.
Application
(S)-3-Benzyloxycarbonylamino-2-(Boc-amino)propionic acid serves as a key chiral building block for the synthesis of peptide mimetics and β-amino acid derivatives. Its dual protected amine functionality—benzyloxycarbonyl (Cbz) at the α-position and tert-butoxycarbonyl (Boc) at the side chain—enables orthogonal deprotection sequences in complex peptide assembly. The molecule exhibits excellent bench stability, facilitates straightforward purification, and participates reliably in standard coupling reactions, making it a practical choice for solid-phase and solution-phase peptide synthesis workflows.
Synthesis
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Route1
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In-stock
76387-70-7 -
501-53-1 - ~96%
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In-stock
65710-57-8
References
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More, Swati S.; Vince, Robert Journal of Medicinal Chemistry, 2009 , vol. 52, # 15 p. 4650 - 4656
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Route2
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In-stock
76387-70-7
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1885-14-9
- ~93%
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In-stock
65710-57-8
References
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Cephalon, Inc. Patent: US2006/189806 A1, 2006 ; Location in patent: Page/Page column 44 ;
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Route3
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916426-81-8
- ~90%
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In-stock
65710-57-8
References
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Teng, Hanbing; Jiang, Zhengguo; Wu, Lamei; Su, Jiangtao; Feng, Xichun; Qiu, Guofu; Liang, Shucai; Hu, Xianming Synthetic Communications, 2006 , vol. 36, # 24 p. 3803 - 3807
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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 113.96
- LogP 1.8907
- H_Acceptors 5
- H_Donors 3
- Rotatable_Bonds 6
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Key Words
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