N-((Benzyloxy)carbonyl)-O-(tert-butyl)-L-threonine

Name: N-((Benzyloxy)carbonyl)-O-(tert-butyl)-L-threonine
Brand: ChemScene
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CAS No. 16966-09-9
Cat. No. CS-0062362
Purity≥96%
MDL No.MFCD06248909

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N-((Benzyloxy)carbonyl)-O-(tert-butyl)-L-threonine|CS-0062362

Structure of 16966-09-9

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General Information

CAS No. 16966-09-9
Cat. No. CS-0062362
Purity ≥96%
MDL No. MFCD06248909
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₂₃NO₅
Molecular Weight None
Synonym(s) None
SMILES C[C@@H](OC(C)(C)C)[C@@H](C(O)=O)NC(OCC1=CC=CC=C1)=O

Description

N-((Benzyloxy)carbonyl)-O-(tert-butyl)-L-threonine serves as a protected amino acid building block for peptide synthesis, featuring orthogonal protection of both the amine and hydroxyl functionalities. The benzyloxycarbonyl group enables selective deprotection under mild hydrogenolysis conditions, while the tert-butyl ester remains intact. This combination streamlines sequential coupling steps in complex peptide assembly, offering enhanced stability and compatibility with standard synthetic protocols.

Application

N-((Benzyloxy)carbonyl)-O-(tert-butyl)-L-threonine serves as a versatile dipeptide building block for peptide synthesis, combining orthogonal protection of both amine and hydroxyl functionalities. The Cbz group enables efficient removal under mild hydrogenolysis conditions, while the tert-butyl ester is stable to basic and nucleophilic reagents yet cleavable with strong acids. This dual protection scheme facilitates sequential coupling strategies and simplifies purification in complex peptide assembly workflows.

Synthesis

Route1
- 52785-41-8
- ~%
- In-stock
  
  16966-09-9
References
- Nakajima, Kiichiro; Neya, Masahiro; Yamada, Shinichi; Okawa, Kenji Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 9 p. 3049 - 3050
Route2
- In-stock
  
  57224-63-2
- ~%
- In-stock
  
  16966-09-9
References
- Schroeder,E. Justus Liebigs Annalen der Chemie, 1963 , vol. 670, p. 127 - 136
Route3
- 14437-51-5
- ~%
- In-stock
  
  16966-09-9
References
- Trzeciak, Arnold; Bannwarth, Willi Synthesis, 1996 , # 12 p. 1433 - 1434

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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Computational Chemistry Data

TPSA 84.86
LogP 2.5696
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Threonine and derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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N-((Benzyloxy)carbonyl)-O-(tert-butyl)-L-threonine

CAS No. 16966-09-9

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