(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)carbonyl)amino)propanoic acid

Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)carbonyl)amino)propanoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 204316-36-9
Cat. No. CS-W009641
Purity≥98%
MDL No.MFCD00273467

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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)carbonyl)amino)propanoic acid|CS-W009641

Structure of 204316-36-9

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General Information

CAS No. 204316-36-9
Cat. No. CS-W009641
Purity ≥98%
MDL No. MFCD00273467
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₄N₂O₆
Molecular Weight 460.48
Synonym(s) Fmoc-Dap(Z)-OH
SMILES O=C(O)[C@H](CNC(OCC1=CC=CC=C1)=O)NC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O

Description

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)carbonyl)amino)propanoic acid is a chiral dipeptide building block featuring orthogonal protection. The fluorenylmethoxycarbonyl (Fmoc) group enables selective N-terminal deprotection under mild basic conditions, while the benzyloxycarbonyl (Boc) moiety provides stable side-chain protection. This combination supports efficient solid-phase peptide synthesis with high fidelity and minimal epimerization.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)carbonyl)amino)propanoic acid serves as a key chiral building block in peptide synthesis, enabling efficient Nα- and side-chain protection. The Fmoc group ensures orthogonal deprotection under mild basic conditions, while the Cbz moiety provides stable protection for the β-amino group. This diprotected amino acid exhibits excellent bench stability, facilitates straightforward purification by chromatography, and functions reliably in solid-phase and solution-phase coupling protocols.

Synthesis

Route1
- 918428-71-4
- ~83%
- In-stock
  
  204316-36-9
References
- Rao, R. V. Ramana; Tantry, Subramanyam J.; Babu, Vommina V. Suresh Synthetic Communications, 2006 , vol. 36, # 19 p. 2901 - 2912
Route2
- 918428-65-6
- ~%
- In-stock
  
  204316-36-9
References
- Synthetic Communications, , vol. 36, # 19 p. 2901 - 2912
Route3
- In-stock
  
  136083-57-3
- ~%
- In-stock
  
  204316-36-9
References
- Synthetic Communications, , vol. 36, # 19 p. 2901 - 2912

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 113.96
LogP 3.9047
H_Acceptors 5
H_Donors 3
Rotatable_Bonds 8

Other Classifications

Building Blocks Functional Group Fmoc

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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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)carbonyl)amino)propanoic acid

CAS No. 204316-36-9

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