(R)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid

Name: (R)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid
Brand: ChemScene
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CAS No. 1018899-99-4
Cat. No. CS-0089163
Molecule weight367.44
Purity≥96%
MDL No.None

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(R)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid|CS-0089163

Structure of 1018899-99-4

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General Information

CAS No. 1018899-99-4
Cat. No. CS-0089163
Purity ≥96%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₂H₂₅NO₄
Molecular Weight 367.44
Synonym(s) FMoc-(R)-2-(aMinoMethyl)-4-Methylpentanoic acid
SMILES CC(C)C[C@H](CNC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)C(O)=O

Description

This fluoren-9-ylmethoxycarbonyl (Fmoc)-protected amino acid derivative features a chiral (R)-configuration at the α-carbon, enabling stereoselective peptide synthesis. The bulky fluoren-9-ylmethyl group enhances solubility and stability during solid-phase assembly, while the pendant methyl-substituted aliphatic chain provides steric differentiation. This combination supports efficient coupling and minimizes racemization under standard conditions.

Application

(R)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid serves as a robust chiral building block for peptide synthesis, offering high stereoselectivity and bench stability. The Fmoc group enables efficient N-terminal protection with orthogonal deprotection under mild basic conditions, while the aliphatic side chain supports diverse functionalization. Its compatibility with standard coupling protocols and ease of purification make it ideal for solid-phase and solution-phase peptide assembly.

Synthesis

Route1
- In-stock
  
  82911-69-1
- In-stock
  
  210345-89-4
- ~45%
- In-stock
  
  1018899-99-4
References
- Reyes-Rangel, Gloria; Jimenez-Gonzalez, Erika; Olivares-Romero, Jose Luis; Juaristi, Eusebio Tetrahedron Asymmetry, 2008 , vol. 19, # 24 p. 2839 - 2849
Route2
- 118053-31-9
- ~%
- In-stock
  
  1018899-99-4
References
- Lee, Hee-Seung; Park, Jin-Seong; Kim, Byeong Moon; Gellman, Samuel H. Journal of Organic Chemistry, 2003 , vol. 68, # 4 p. 1575 - 1578
Route3
- 501330-86-5
- ~%
- In-stock
  
  1018899-99-4
References
- Lee, Hee-Seung; Park, Jin-Seong; Kim, Byeong Moon; Gellman, Samuel H. Journal of Organic Chemistry, 2003 , vol. 68, # 4 p. 1575 - 1578

Safety Information

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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 75.63
LogP 4.272
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 7

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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(R)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-4-methylpentanoic acid

CAS No. 1018899-99-4

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