(R)-2-(((Benzyloxy)carbonyl)amino)-3-(tritylthio)propanoic acid

Name: (R)-2-(((Benzyloxy)carbonyl)amino)-3-(tritylthio)propanoic acid
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CAS No. 26311-04-6
Cat. No. CS-0527224
Purity≥98%
MDL No.None

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(R)-2-(((Benzyloxy)carbonyl)amino)-3-(tritylthio)propanoic acid|CS-0527224

Structure of 26311-04-6

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Description

(R)-2-(((Benzyloxy)carbonyl)amino)-3-(tritylthio)propanoic acid features a chiral backbone with orthogonal protection: the Nα-benzyloxycarbonyl group enables controlled peptide coupling, while the tritylthio side chain offers robust, selectively removable sulfur anchoring. This dual protection strategy supports efficient synthesis of cysteine-containing peptides under mild conditions.

Application

(R)-2-(((Benzyloxy)carbonyl)amino)-3-(tritylthio)propanoic acid serves as a robust chiral building block for peptide synthesis, offering orthogonal protection of the α-amino and thiol functionalities. The benzyloxycarbonyl (Cbz) group enables mild deprotection under hydrogenolysis, while the tritylthio group provides exceptional stability and selective removal via acidolysis. Its bench-stable nature and compatibility with standard coupling protocols facilitate efficient assembly of cysteine-containing peptides and complex heterocyclic scaffolds.

General Information

CAS No. 26311-04-6
Cat. No. CS-0527224
Purity ≥98%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₀H₂₇NO₄S
Molecular Weight 497.60
Synonym(s) N-α-Carbobenzoxy-S-trityl-L-cysteine
SMILES O=C(OCC1=CC=CC=C1)N[C@H](C(O)=O)CSC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4

Computational Chemistry Data

TPSA 75.63
LogP 6.0913
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 10

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-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

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Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Cysteine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-2-(((Benzyloxy)carbonyl)amino)-3-(tritylthio)propanoic acid

CAS No. 26311-04-6

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