4-Amino-1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidin-2(1H)-one

Name: 4-Amino-1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidin-2(1H)-one
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CAS No. 666848-11-9
Cat. No. CS-0160913
Purity≥97%
MDL No.MFCD09264239

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4-Amino-1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidin-2(1H)-one|CS-0160913

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General Information

CAS No. 666848-11-9
Cat. No. CS-0160913
Purity ≥97%
MDL No. MFCD09264239
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₆IN₃O₄Si
Molecular Weight 467.37
Synonym(s) 5-TBDMS-5-I-2-dC
SMILES O[C@H]1C[C@H](N2C(N=C(N)C(I)=C2)=O)O[C@@H]1CO[Si](C)(C)C(C)(C)C

Description

This pyrimidinone derivative features a sterically shielded silyl-protected hydroxyl group and a reactive iodine at C5, enabling selective late-stage functionalization. The 4-amino substituent enhances electron density for coupling reactions, while the tetrahydrofuran ring imparts conformational rigidity. Designed for nucleoside analog synthesis, it offers improved stability and solubility under standard conditions.

Application

4-Amino-1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidin-2(1H)-one serves as a key building block for nucleoside analog synthesis, enabling efficient late-stage functionalization in medicinal chemistry. The tert-butyldimethylsilyl (TBS) group provides robust protection of the hydroxyl moiety, offering excellent bench stability and compatibility with standard deprotection protocols. The iodopyrimidine core facilitates transition-metal-catalyzed cross-coupling reactions, while the amino and hydroxyl functionalities allow for orthogonal derivatization. This compound functions reliably in solid-phase synthesis and solution-phase assembly of complex heterocyclic scaffolds.

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 99.6
LogP 2.1003
H_Acceptors 7
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Life Science Nucleosides & Nucleotides Nucleosides, Deoxyribonucleosides and Other Nucleosides

Biochemistry Biochemicals and Reagents Nucleosides, Nucleotides, Oligonucleotides Nucleobases and their Analogs

Biochemistry Biochemicals and Reagents Nucleosides, Nucleotides, Oligonucleotides Nucleoside Analogs

Biochemistry Biochemicals and Reagents Nucleosides, Nucleotides, Oligonucleotides Nucleosides

Catalysis Compounds by Element Classes Metal Compounds Semimetal Compounds

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4-Amino-1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidin-2(1H)-one

CAS No. 666848-11-9

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