tert-Butyl (S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-hydroxybutanoate

Name: tert-Butyl (S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-hydroxybutanoate
Brand: ChemScene
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CAS No. 133565-45-4
Cat. No. CS-0148367
Purity≥98%
MDL No.None

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tert-Butyl (S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-hydroxybutanoate|CS-0148367

Structure of 133565-45-4

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General Information

CAS No. 133565-45-4
Cat. No. CS-0148367
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₃H₂₇NO₅
Molecular Weight 397.46
Synonym(s) (S)-tert-Butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-hydroxybutanoate
SMILES O=C(OC(C)(C)C)C[C@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CO

Description

This fluoren-9-ylmethoxycarbonyl-protected hydroxyproline derivative features a stereodefined (S)-configuration and a bench-stable tert-butyl ester, enabling direct incorporation into peptide chains under standard coupling conditions. The orthogonal protecting groups facilitate selective deprotection during synthetic workflows.

Application

tert-Butyl (S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-hydroxybutanoate serves as a protected hydroxy amino acid building block for peptide synthesis, enabling the incorporation of (S)-4-hydroxyproline motifs. The Fmoc group provides orthogonal protection for the amine, while the tert-butyl ester allows selective deprotection under mild acidic conditions. Its bench-stable nature and compatibility with standard coupling protocols facilitate efficient solid-phase and solution-phase peptide assembly.

Synthesis

Route1
- In-stock
  
  71989-14-5
- ~95%
- In-stock
  
  133565-45-4
References
- Boeijen; Van Ameijde; Liskamp Journal of Organic Chemistry, 2001 , vol. 66, # 25 p. 8454 - 8462
Route2
- 86061-01-0
- ~90%
- In-stock
  
  133565-45-4
References
- Papavassilopoulou, Eleni; Christofis, Petros; Terzoglou, Despina; Moutevelis-Minakakis, Panagiota Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8323 - 8325
Route3
- 146803-45-4
- ~68%
- In-stock
  
  133565-45-4
References
- Chen, Jack J.; Aduda, Vince Synthetic Communications, 2007 , vol. 37, # 20 p. 3493 - 3499

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 84.86
LogP 3.6178
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Amine

Building Blocks Functional Group Alcohol

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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tert-Butyl (S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-hydroxybutanoate

CAS No. 133565-45-4

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