N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-D-homoserine

Name: N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-D-homoserine
Brand: ChemScene
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CAS No. 1301706-79-5
Cat. No. CS-0162221
Purity≥98%
MDL No.None

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N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-D-homoserine|CS-0162221

Structure of 1301706-79-5

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Description

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-D-homoserine is a protected amino acid derivative featuring a fluorenylmethoxycarbonyl (Fmoc) group at the α-amino position and a benzyl ether protecting group on the hydroxyl moiety. This combination enables orthogonal protection during peptide synthesis, offering enhanced stability under basic conditions and facilitating selective deprotection. The Fmoc group allows for mild removal via base treatment, while the O-benzyl protection remains intact, enabling sequential coupling strategies in complex peptide assembly. Designed for use in solid-phase and solution-phase syntheses, this reagent streamlines the incorporation of D-homoserine into target sequences with high fidelity.

Application

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-D-homoserine serves as a robust chiral building block for peptide synthesis, enabling efficient incorporation of D-homoserine residues with high fidelity. The Fmoc group provides orthogonal protection for the amine, while the O-benzyl moiety stabilizes the hydroxyl functionality under standard coupling conditions. This derivative exhibits excellent bench stability, facilitates straightforward purification, and is compatible with diverse coupling protocols in both solution-phase and solid-phase synthesis workflows.

General Information

CAS No. 1301706-79-5
Cat. No. CS-0162221
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₅NO₅
Molecular Weight 431.48
Synonym(s) N-α-(9-Fluorenylmethoxycarbonyl)-O-benzyl-D-homoserine
SMILES O=C(O)[C@@H](CCOCC1=CC=CC=C1)NC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O

Computational Chemistry Data

TPSA 84.86
LogP 4.5852
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 9

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-P330-P362+P364-P405-P501

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Other Classifications

Building Blocks Functional Group Ether

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Serine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-benzyl-D-homoserine

CAS No. 1301706-79-5

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