144872-52-6

Basic information

• Product Name: 1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4-(1H,3H)dione
• Synonyms: 1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4-(1H,3H)dione
• CAS NO: 144872-52-6
• Molecular Weight: 592.506
• Mol File: 144872-52-6.mol

Chemical Properties

• CAS DataBase Reference: 1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4-(1H,3H)dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4-(1H,3H)dione(144872-52-6)
• EPA Substance Registry System: 1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4-(1H,3H)dione(144872-52-6)

Safety Data

• Hazardous Substances Data: 144872-52-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4-(1H,3H)dione is used as a synthetic intermediate for the creation of more complex molecules in the field of organic chemistry. Its unique structure and functional groups make it a valuable building block for the development of novel compounds with specific properties and applications.
Used in Medicinal Chemistry Research:
In the pharmaceutical industry, 1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4-(1H,3H)dione is used as a substrate or reagent for the synthesis of new drugs and therapeutic agents. The presence of the iodine atom and the chiral center with a 2R,4S,5R configuration may provide opportunities for the development of enantiomerically pure drugs with improved efficacy and reduced side effects.
Used in Chemical Protection Groups:
The tert-butyldiphenylsilyl group in 1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4-(1H,3H)dione makes it useful as a protective group for alcohol or hydroxyl groups during sensitive chemical reactions. This application is particularly relevant in the synthesis of complex natural products and pharmaceuticals, where the selective protection of functional groups is crucial for achieving the desired product outcome.

Upstream product

• 54-42-2 5-Iodo-2'-deoxyuridine 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 117626-99-0 3'-O-Acetyl-2'-deoxy-5-ethynyluridine 
• 144872-57-1 3'-Benzoyl-5'-(N-diethoxyphosphoryl)sulfamoyl-5-iodo-2'-deoxyuridine 
• 144872-59-3 3'-Benzoyl-5-iodo-5'-O-sulfamoylcarbamoyl-2'-deoxyuridine 
• 144872-55-9 3'-Benzoyl-5-iodo-5'-sulfamoyl-2'-deoxyuridine 
• 144872-54-8 3'-O-bezoyl-2'-deoxy-5-iodouridine 
• 144872-53-7 3'-Benzoyl-5'-tert-butyldiphenylsilyl-5-iodo-2'-deoxyuridine 

Relevant articles and documents

Development of ethynyl-2′-deoxyuridine chemical probes for cell proliferation

A common method of evaluating cellular proliferation is to label DNA with chemical probes. 5-Ethynyl-2′-deoxyuridine (EdU) is a widely utilized chemical probe for labeling DNA, and upon incorporation, EdU treatment of cells is followed by a reaction with a small molecule fluorescent azide to allow detection. The limitations when using EdU include cytotoxicity and a reliance on nucleoside active transport mechanisms for entry into cells. Here we have developed six novel EdU pro-labels that consist of EdU modified with variable lipophilic acyl ester moieties. This pro-label:chemical probe relationship parallels the prodrug:drug relationship that is employed widely in medicinal chemistry. EdU and EdU pro-labels were evaluated for their labeling efficacy and cytotoxicity. Several EdU pro-label analogues incorporate into DNA at a similar level to EdU, suggesting that nucleoside transporters can be bypassed by the pro-labels. These EdU pro-labels also had reduced toxicity compared to EdU.

OLIGONUCLEOTIDE AND NUCLEIC ACID SYNTHESIS

The present invention relates to methods for the high fidelity synthesis of oligonucleotides and polynucleotides on a solid surface. In particular, the invention relates to methods of synthesising oligonucleotides, polynucleotides, and doublestranded polynucleotides/nucleic acids, such as DNA and XNA, wherein the process comprises thermally controlled deprotection steps at the 5'-OH of previously coupled nucleosides or nucleotides at selected sites on the surface of the substrate.

METHODS OF SYNTHESIZING LABELED NUCLEOSIDES

Disclosed herein, inter alia, are compounds, compositions, and methods of synthesizing labeled nucleosides.

THERMALLY-CLEAVABLE PROTECTING AND LINKER GROUPS

The present invention relates to chemical linkers and protecting groups, compounds and compositions containing the chemical linkers or protecting groups, and intermediates and processes that can be used to prepare them. The chemical linkers and protecting groups are based on pyrrolidine and piperidine activating groups, which undergo intramolecular cyclisation upon heating with release of carbon dioxide, thereby releasing the organic compound from a substrate. In particular, those chemical linkers and protecting groups are useful in the solid phase synthesis of oligonucleotides according to the following representative schemes.

Synthesis of Analogues of 5-Iodo-2'-deoxyuridine-5'-diphosphate

The synthesis of three types of diphosphate analogues of 5-iodo-2'-deoxyuridine-5'-diphosphate is reported.Routes are described to the 5'-phosphonoacetamido, the 5'-N-phosphonosulfamoyl and the 5'-O-sulfamoylcarbamoyl derivatives, 2, 3 and 4 starting from