N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-serine

Name: N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-serine
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CAS No. 146346-81-8
Cat. No. CS-0101001
Purity≥95%
MDL No.MFCD02092931

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N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-serine|CS-0101001

Structure of 146346-81-8

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General Information

CAS No. 146346-81-8
Cat. No. CS-0101001
Purity ≥95%
MDL No. MFCD02092931
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₃₁NO₅Si
Molecular Weight 441.59
Synonym(s) None
SMILES O=C(O)[C@H](CO[Si](C)(C(C)(C)C)C)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

This fluorenylmethoxycarbonyl-protected serine derivative features a tert-butyldimethylsilyl group that enhances stability and solubility during peptide synthesis. The orthogonal protection scheme enables selective deprotection, streamlining the incorporation of serine residues in complex sequences under standard conditions.

Application

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-serine serves as a bifunctional amino acid building block for peptide synthesis, enabling orthogonal protection of both the α-amino and hydroxyl side chain functionalities. The Fmoc group facilitates mild base-labile deprotection, while the TBDMS ether provides robust protection against nucleophiles and acidic conditions. Its bench-stable nature and compatibility with standard coupling protocols streamline sequence assembly and support efficient purification.

Synthesis

Route1
- 18162-48-6
- ~%
- In-stock
  
  146346-81-8
References
- Fischer, Peter M. Tetrahedron Letters, 1992 , vol. 33, # 49 p. 7605 - 7608
Route2
- In-stock
  
  73724-45-5
- ~%
- In-stock
  
  146346-81-8
References
- Fischer, Peter M. Tetrahedron Letters, 1992 , vol. 33, # 49 p. 7605 - 7608
Route3
- In-stock
  
  82911-69-1
- 126027-32-5
- ~%
- In-stock
  
  146346-81-8
References
- Luo, Yue; Evindar, Ghotas; Fishlock, Dan; Lajoie, Gilles A Tetrahedron Letters, 2001 , vol. 42, # 23 p. 3807 - 3809

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 84.86
LogP 5.0001
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 7

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Serine and derivatives

Building Blocks Functional Group Fmoc

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-serine

CAS No. 146346-81-8

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