(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

Name: (R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid
Brand: ChemScene
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CAS No. 109745-15-5
Cat. No. CS-0148631
Molecule weight425.47
Purity≥98%
MDL No.MFCD00077054

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(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid|CS-0148631

Structure of 109745-15-5

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General Information

CAS No. 109745-15-5
Cat. No. CS-0148631
Purity ≥98%
MDL No. MFCD00077054
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₇NO₆
Molecular Weight 425.47
Synonym(s) Fmoc-D-Glu-OtBu
SMILES O=C(O)CC[C@H](C(OC(C)(C)C)=O)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

This fluoren-9-ylmethoxycarbonyl-protected amino acid derivative features a chiral (R)-configuration at the C4 position, enabling stereocontrolled peptide synthesis. The tert-butoxy carbonyl group provides enhanced stability and selective deprotection under mild acidic conditions, while the fluoren-9-ylmethoxycarbonyl moiety facilitates efficient coupling and purification.

Application

(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid serves as a key chiral building block for peptide synthesis and heterocyclic scaffold construction. Its protected α-amino ketone functionality enables selective transformations under mild conditions, while the Fmoc group ensures stability and easy removal during deprotection. The tert-butoxy carbonyl moiety provides orthogonal protection, facilitating sequential functionalization in complex molecule assembly.

Synthesis

Route1
- In-stock
  
  6893-26-1
- ~%
- In-stock
  
  109745-15-5
References
- Tetrahedron Letters, , vol. 38, # 29 p. 5229 - 5232
Route2
- 746581-15-7
- ~%
- In-stock
  
  109745-15-5
References
- Tetrahedron Letters, , vol. 38, # 29 p. 5229 - 5232

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 101.93
LogP 4.1002
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 7

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Glutamic acid and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

CAS No. 109745-15-5

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