N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-N-methyl-L-threonine

Name: N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-N-methyl-L-threonine
Brand: ChemScene
Availability: InStock
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CAS No. 198561-81-8
Cat. No. CS-0089858
Purity≥95%
MDL No.MFCD00235882

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N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-N-methyl-L-threonine|CS-0089858

Structure of 198561-81-8

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General Information

CAS No. 198561-81-8
Cat. No. CS-0089858
Purity ≥95%
MDL No. MFCD00235882
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₇H₂₇NO₅
Molecular Weight 445.51
Synonym(s) None
SMILES C[C@@H](OCC1=CC=CC=C1)[C@@H](C(O)=O)N(C(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O)C

Description

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-N-methyl-L-threonine is a protected amino acid derivative featuring orthogonal functional group shielding. The Fmoc group enables selective N-terminal deprotection in peptide synthesis, while the O-benzyl and N-methyl modifications enhance stability and modulate reactivity. This configuration supports efficient coupling under standard conditions, streamlining the assembly of complex peptide sequences with minimal side-product formation.

Application

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-N-methyl-L-threonine serves as a protected amino acid building block for peptide synthesis, enabling orthogonal protection of hydroxyl and amine functionalities. The Fmoc group facilitates mild base-labile deprotection, while the O-benzyl and N-methyl groups provide enhanced stability and resistance to side reactions. This derivative supports efficient coupling protocols and simplifies purification in complex peptide sequences.

Synthesis

Route1
- 1140836-81-2
- ~82%
- In-stock
  
  198561-81-8
References
- Aurelio, Luigi; Brownlee, Robert T. C.; Hughes, Andrew B. Australian Journal of Chemistry, 2008 , vol. 61, # 8 p. 615 - 629
Route2
- 1140836-81-2
- ~86%
- In-stock
  
  198561-81-8
References
- Aurelio, Luigi; Brownlee, Robert T. C.; Hughes, Andrew B. Australian Journal of Chemistry, 2008 , vol. 61, # 8 p. 615 - 629

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-P280-P302+P352

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Computational Chemistry Data

TPSA 76.07
LogP 4.9258
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 8

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Threonine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-N-methyl-L-threonine

CAS No. 198561-81-8

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