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

Name: (R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 204251-86-5
Cat. No. CS-0157986
Purity≥95%
MDL No.MFCD01074691

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(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid|CS-0157986

Structure of 204251-86-5

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General Information

CAS No. 204251-86-5
Cat. No. CS-0157986
Purity ≥95%
MDL No. MFCD01074691
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₃H₂₃NO₆
Molecular Weight 409.43
Synonym(s) N-Fmoc-D-glutamic acid 1-allyl ester
SMILES C=CCOC([C@H](NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O)CCC(O)=O)=O

Description

This chiral fluorenonyl-protected amino acid derivative features a bench-stable, electron-rich fluoren-9-ylmethyl carbamate group that enables efficient solid-phase peptide synthesis. The allyloxy-substituted ketone side chain provides a handle for orthogonal functionalization via olefin metathesis, while the (R)-stereochemistry ensures high fidelity in peptide coupling reactions.

Application

(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid serves as a versatile chiral building block for peptide and peptidomimetic synthesis, enabling efficient incorporation of allyl-protected hydroxyl functionalities. The fluorenylmethoxycarbonyl (Fmoc) group provides robust protection for primary amines during solid-phase synthesis, while the allyloxy substituent offers orthogonal handle for subsequent functionalization via palladium-catalyzed reactions. Bench-stable and amenable to standard purification methods, it facilitates reliable access to complex scaffolds in medicinal chemistry campaigns.

Synthesis

Route1
- In-stock
  
  104091-08-9
- 106-95-6
- ~89%
- In-stock
  
  204251-86-5
References
- Fluxa, Viviana S.; Maillard, Noelie; Page, Malcolm G. P.; Reymond, Jean-Louis Chemical Communications, 2011 , vol. 47, # 5 p. 1434 - 1436
Route2
- In-stock
  
  104091-08-9
- ~%
- In-stock
  
  204251-86-5
References
- O'Brien, Dominic P.; Entress, Richard M. H.; Cooper, Matthew A.; O'Brien, Simon W.; Hopkinson, Andrew; Williams, Dudley H. Journal of the American Chemical Society, 1999 , vol. 121, # 22 p. 5259 - 5265
Route3
- 1269619-44-4
- ~%
- In-stock
  
  204251-86-5
References
- Agnihotri, Geetanjali; Ukani, Rehman; Malladi, Subbalakshmi S.; Warshakoon, Hemamali J.; Balakrishna, Rajalakshmi; Wang, Xinkun; David, Sunil A. Journal of Medicinal Chemistry, 2011 , vol. 54, # 5 p. 1490 - 1510

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 3.4877
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 9

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Olefins

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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

CAS No. 204251-86-5

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