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

Name: N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-homoserine
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CAS No. 1333332-17-4
Cat. No. CS-0148544
Purity≥95%
MDL No.MFCD30529785

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N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-homoserine|CS-0148544

Structure of 1333332-17-4

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General Information

CAS No. 1333332-17-4
Cat. No. CS-0148544
Purity ≥95%
MDL No. MFCD30529785
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₅H₃₃NO₅Si
Molecular Weight 455.62
Synonym(s) N-Fmoc-O-TBDMS-L-homoserine
SMILES O=C(O)[C@H](CCO[Si](C)(C(C)(C)C)C)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-homoserine features a fluorenylmethoxycarbonyl group for efficient peptide coupling and a tert-butyldimethylsilyl moiety for selective hydroxyl protection. This bifunctional derivative enables robust, orthogonal protection in synthetic peptide and oligonucleotide workflows.

Application

N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-homoserine serves as a protected amino acid building block for peptide synthesis, combining orthogonal protection of the amine (Fmoc) and hydroxyl (TBDMS) functionalities. The Fmoc group enables mild base-mediated deprotection, while the TBDMS ether offers stability under acidic and basic conditions, facilitating selective transformations. This derivative simplifies purification and enhances solubility in organic solvents, making it ideal for solid-phase and solution-phase peptide coupling protocols requiring precise functional group management.

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-P280-P302+P352

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Computational Chemistry Data

TPSA 84.86
LogP 5.3902
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 8

Other Classifications

Building Blocks Functional Group Organosilicon compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Serine and derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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

CAS No. 1333332-17-4

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