N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-allylglycine

Name: N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-allylglycine
Brand: ChemScene
Availability: InStock
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CAS No. 222725-35-1
Cat. No. CS-0089995
Purity≥97%
MDL No.MFCD17976766

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-allylglycine|CS-0089995

Structure of 222725-35-1

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General Information

CAS No. 222725-35-1
Cat. No. CS-0089995
Purity ≥97%
MDL No. MFCD17976766
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₁₉NO₄
Molecular Weight None
Synonym(s) None
SMILES O=C(O)CN(C(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CC=C

Description

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-allylglycine is a protected amino acid derivative featuring a fluorenylmethyl carbamate (Fmoc) group and a reactive allyl side chain. This combination enables orthogonal protection strategies in peptide synthesis, where the Fmoc moiety facilitates base-labile deprotection and the allyl group supports mild, chemoselective removal via palladium-catalyzed reactions. The molecule integrates seamlessly into solid-phase workflows, offering reliable handling and compatibility with diverse coupling conditions.

Application

N-((9H-Fluoren-9-yl)methoxy)carbonyl)-N-allylglycine serves as a versatile protected amino acid building block for peptide synthesis, enabling orthogonal handling of the allyl group and Fmoc moiety. The allyl side chain facilitates post-coupling modifications via palladium-catalyzed reactions, while the Fmoc group ensures efficient deprotection under mild basic conditions. This dual functionality supports streamlined synthetic sequences in complex peptide and peptidomimetic assembly.

Synthesis

Route1
- In-stock
  
  82911-69-1
- 3182-78-3
- ~77%
- In-stock
  
  222725-35-1
References
- Schmidt, Boris; Patzke, Greta R. Synthetic Communications, 1999 , vol. 29, # 6 p. 1025 - 1032
Route2
- 3182-79-4
- In-stock
  
  82911-69-1
- ~95%
- In-stock
  
  222725-35-1
References
- Reichwein, John F.; Liskamp, Rob M. J. European Journal of Organic Chemistry, 2000 , # 12 p. 2335 - 2344
Route3
- In-stock
  
  82911-69-1
- 10552-80-4
- ~%
- In-stock
  
  222725-35-1
References
- Liu, Fa; Stephen, Andrew G.; Waheed, Abdul A.; Freed, Eric O.; Fisher, Robert J.; Burke Jr., Terrence R. Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 1 p. 318 - 321

Safety Information

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GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 66.84
LogP 3.5081
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 6

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Glycine and derivatives

Building Blocks Functional Group Fmoc

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)-N-allylglycine

CAS No. 222725-35-1

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