51549-29-2

Basic information

• Product Name: 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine
• Synonyms: 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine
• CAS NO: 51549-29-2
• Molecular Formula: C₂₁H₄₁N₃O₄Si₂
• Molecular Weight: 455.73894
• Product Categories: Aromatics, Heterocycles, Nucleotides, Bases & Related Reagents, Sulfur & Selenium Compounds
• Mol File: 51549-29-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Dimethylsulfoxide, Ethylacetate
• CAS DataBase Reference: 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine(51549-29-2)
• EPA Substance Registry System: 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine(51549-29-2)

Safety Data

• Hazardous Substances Data: 51549-29-2(Hazardous Substances Data)

Usage

Description

2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine is a chemical compound that serves as an intermediate in the biosynthesis of cholyl-CoA and oligodeoxyribonucleotides. It is a white solid with significant applications in various fields due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine is used as an intermediate for the biosynthesis of cholyl-CoA, which plays a crucial role in the synthesis of bile acids and cholesterol. This application is essential for understanding and potentially treating various liver and metabolic disorders.
Used in Biotechnology Industry:
In the biotechnology industry, 2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine is used as an intermediate for the biosynthesis of oligodeoxyribonucleotides. These are short DNA fragments that have applications in genetic research, diagnostics, and the development of new therapeutic strategies, such as gene silencing and antisense therapies.
Used in Chemical Synthesis:
2',3'-Di-O-(tert-butyldiMethylsilyl)-2'-deoxycytidine is also used as a key intermediate in the synthesis of various chemical compounds, particularly those with potential applications in the pharmaceutical and biotechnology industries. Its unique chemical properties make it a valuable building block for the development of new drugs and other bioactive molecules.

Upstream product

• 41251-37-0 methyl-d3-magnesium iodide 
• 478843-96-8 5-iodo-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxycytidine 

Downstream Products

• 154738-03-1 3',5'-O-[bis-(tert-butyldimethylsilyl)]-4-N-(triphenylmethylsulfenyl)deoxycytidine 
• 104006-66-8 C₆₁H₆₇N₃O₁₀Si₂ 
• 205238-86-4 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-4-(2-nitro-phenylsulfanylamino)-1H-pyrimidin-2-one 
• 203259-04-5 1-Benzoyl-3-{1-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-thiourea 
• 51549-38-3 N⁴-benzoyl-O^3',O^5'-bis(tert-butyldimethylsilyl)-2'-deoxycytidine 
• 51549-28-1 3'-O-(tert-butyldimethylsilyl)-2'-deoxycytidine 
• 828261-34-3 {1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid phenyl ester 
• 828261-40-1 1-(1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-3-quinolin-5-yl-urea 
• 691880-72-5 5'-O-monomethoxytrityl-2'-deoxycytidine dimethylsulfilimine 
• 691880-73-6 5'-O-monomethoxytrityl-2'-deoxycytidine dimethylsulfilimine 3'-H-phosphonate 
• 4836-13-9 N₄-benzoyl-2'-deoxycytidine 
• 111447-33-7 3-(2-hydroxyethyl)-2'-deoxyuridine 
• 203259-05-6 N-Benzoyl-N'-{1-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-guanidine 
• 205238-92-2 N-{1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-N-(2-nitro-phenylsulfanyl)-acetamide 

Relevant articles and documents

Biomimetic Iron Complex Achieves TET Enzyme Reactivity**

The epigenetic marker 5-methyl-2′-deoxycytidine (5mdC) is the most prevalent modification to DNA. It is removed inter alia via an active demethylation pathway: oxidation by Ten-Eleven Translocation 5-methyl cytosine dioxygenase (TET) and subsequent removal via base excision repair or direct demodification. Recently, we have shown that the synthetic iron(IV)-oxo complex [FeIV(O)(Py5Me2H)]2+ (1) can serve as a biomimetic model for TET by oxidizing the nucleobase 5-methyl cytosine (5mC) to its natural metabolites. In this work, we demonstrate that nucleosides and even short oligonucleotide strands can also serve as substrates, using a range of HPLC and MS techniques. We found that the 5-position of 5mC is oxidized preferably by 1, with side reactions occurring only at the strand ends of the used oligonucleotides. A detailed study of the reactivity of 1 towards nucleosides confirms our results; that oxidation of the anomeric center (1′) is the most common side reaction.