140712-80-7

Usage

Uses

Used in Organic Synthesis:
N4-BENZOYL-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE is used as a building block in organic synthesis for the production of modified nucleosides and nucleotides. Its unique structure and functional groups contribute to the development of nucleic acid analogs, which are essential for studying biological processes involving cytidine nucleosides.
Used in Nucleic Acid Research:
In the field of nucleic acid research, N4-BENZOYL-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE is utilized as a key component in the development of nucleic acid analogs. These analogs are crucial for understanding the role of cytidine nucleosides in various biological processes and can potentially lead to the discovery of new therapeutic agents.
Used in Molecular Biology and Medicinal Chemistry:
N4-BENZOYL-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE is used in the preparation of oligonucleotides for therapeutic and diagnostic purposes. Its incorporation into oligonucleotide sequences allows for the targeting of specific genetic sequences, making it a valuable tool in molecular biology and medicinal chemistry for the development of novel treatments and diagnostic methods.

Upstream product

• 51549-36-1 N-(1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 4803-92-3 (5'-O,4-N)-dibenzoyl-2'-deoxycytidine 
• 4836-13-9 N₄-benzoyl-2'-deoxycytidine 
• 139244-40-9 N-(1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 869563-54-2 N-{1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 

Downstream Products

• 854389-81-4 {(2R,3S,5R)-5-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-ylmethoxymethyl}-phosphonic acid monomethyl ester 

Relevant academic research and scientific papers

Novel chemoenzymatic protocol for the synthesis of 3′-O- dimethoxytrityl-2′-deoxynucleoside derivatives as building blocks for oligonucleotide synthesis

An easy, efficient, and scalable chemoenzymatic strategy for the synthesis of 3′-O-dimethoxytrityl-2′-deoxynucleosides has been developed. A key feature of this approach is the regioselective synthesis of 5′-O-levulinyl-2′-deoxynucleosides through enzymatic acylation in the presence of Candida antarctica lipase B. In addition, it was observed that the deblocking of levulinyl group from the 5′-position is perfectly compatible with conventional base protecting groups. To demonstrate the scalability of this method, 3′-O-dimethoxytritylthymidine (4a) was synthesized on 25-g scale. These monomers (4a-d) are useful building blocks for the synthesis of oligonucleotides.

Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides

An unique set of 5′-O- and 3′-O-phosphonomethyl derivatives of four natural 2′-deoxyribonucleosides, 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine, 5′-O- and 2′-O-phosphonomethyl derivatives of 1-(3-deoxy-β-D-erythro-pentofuranosyl)thymine, and 1-(3-deoxy-β-D- threo-pentofuranosyl)thymine has been synthesized as a pool of monomers for the synthesis of modified oligonucleotides. The phosphonate moiety was protected with 4-methoxy-1-oxido-2-pyridylmethyl ester group, serving also as an intramolecular catalyst in the coupling step.

Method for purifying protected 2'-deoxycytidines and hydrated crystals thereof

A protected 2′-deoxycytidine is purified by precipitating the protected 2′-deoxycytidine represented by general formula (3) in the form of a hydrated crystal from a solution containing the protected 2′-deoxycytidine and water, and by recovering the protected 2′-deoxycytidine: wherein R1 represents a 4-methoxytrityl, 4,4′-dimethoxytrityl, or triphenylmethyl group; and B1 represents a cytosine group having a protected amino group. The compound represented by general formula (3) is, in particular, a protected 2′-deoxycytidine represented by formula (4): The 2′-deoxycytidine is used as a raw material for antisense DNA.

Synthesis of 3'-azido-3'-deoxythymidine-terminated oligonucleotide

A method of completely chemical synthesis of 3'-azido-3'- deoxythymidine-terminated oligonucleotides via 5'-H-phosphonate of AZT is described.