Fmoc-Glu(OtBu)-OH

CAS No. 71989-18-9
Cat. No. CS-W008588
Molecule weight425.47
Purity≥98%
MDL No.MFCD00037135

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Structure of 71989-18-9

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General Information

CAS No. 71989-18-9
Cat. No. CS-W008588
Purity ≥98%
MDL No. MFCD00037135
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₇NO₆
Molecular Weight 425.47
Synonym(s) None
SMILES O=C(OC(C)(C)C)CC[C@@H](C(O)=O)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid is a chiral building block featuring a fluorenylmethyl carbamate (Fmoc) protecting group and a tert-butyl ester handle. This combination enables orthogonal protection in peptide synthesis, where the Fmoc moiety facilitates base-labile deprotection while the tert-butoxy carbonyl remains stable under acidic conditions. The molecule integrates seamlessly into solid-phase workflows, supporting efficient chain elongation and selective functionalization.

Application

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid serves as a valuable chiral building block for the synthesis of peptide mimetics and β-lactam precursors. Its protected α-amino acid scaffold enables efficient coupling reactions with minimal racemization, while the tert-butoxy carbonyl group provides orthogonal stability under standard deprotection conditions. The fluorenylmethyl (Fmoc) protecting group ensures high compatibility in solid-phase peptide synthesis workflows.

Synthesis

Route1
- 851713-96-7
- ~84%
- In-stock
  
  71989-18-9
References
- Sedighi, Minoo; Lipton, Mark A. Organic Letters, 2005 , vol. 7, # 8 p. 1473 - 1475
Route2
- In-stock
  
  2419-56-9
- In-stock
  
  82911-69-1
- ~60%
- In-stock
  
  71989-18-9
References
- Nowshuddin, Shaik; Rao; Reddy, A. Ram Synthetic Communications, 2009 , vol. 39, # 11 p. 2022 - 2031
Route3
- In-stock
  
  2419-56-9
- In-stock
  
  88744-04-1
- ~93%
- In-stock
  
  71989-18-9
References
- Schoen, Istvan; Kisfaludy, Lajos Synthesis, 1986 , # 4 p. 303 - 305

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

Quality Control

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Computational Chemistry Data

TPSA 101.93
LogP 4.1002
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 7

Other Classifications

Bioactive Molecules Peptides

Building Blocks Functional Group Fmoc

Life Science Amino Acids and their Derivatives Glutamic acid and derivatives

Life Science Amino Acids and their Derivatives N-protected amino acid

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Amino Acid Derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Biochemistry Biochemicals and Reagents Amino Acids N-Protected Amino Acids

Key Words

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Fmoc-Glu(OtBu)-OH

CAS No. 71989-18-9

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