255396-09-9

Basic information

• Product Name: 1-(5-O-dimethyoxytrityl-4-thio-β-D-arabinofuranosyl)cytosine
• Synonyms: 1-(5-O-dimethyoxytrityl-4-thio-β-D-arabinofuranosyl)cytosine
• CAS NO: 255396-09-9
• Molecular Weight: 561.659
• Mol File: 255396-09-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(5-O-dimethyoxytrityl-4-thio-β-D-arabinofuranosyl)cytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-O-dimethyoxytrityl-4-thio-β-D-arabinofuranosyl)cytosine(255396-09-9)
• EPA Substance Registry System: 1-(5-O-dimethyoxytrityl-4-thio-β-D-arabinofuranosyl)cytosine(255396-09-9)

Safety Data

• Hazardous Substances Data: 255396-09-9(Hazardous Substances Data)

Usage

Chemical structure

A derivative of cytosine, a nitrogenous base found in DNA and RNA.

Modified sugar molecule

Contains a β-D-arabinofuranosyl group attached to the cytosine base.

Additional functional group

Contains a 5-O-dimethyoxytrityl-4-thio group linked to the sugar molecule.

Application

Commonly used in the synthesis of nucleoside analogs.

Potential use

May have applications in the field of medicinal chemistry for the development of new pharmaceuticals.

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 26599-17-7 TaraC 

Downstream Products

• 26599-17-7 TaraC 

Relevant articles and documents

Chemical and enzymatic synthesis of 4′-thio-β-D- arabinofuranosylcytosine monophosphate and triphosphate

N4-Acetyl-1-(2, 3-di-O-acetyl-4-thio-β-D-arabinofuranosyl) cytosine (2) was synthesized in three steps from 1-(4-thio-β-D- arabinofuranosyl)cytosine (1). The reaction of this partially blocked 4′-thio-ara-C derivative 2 with 2-chloro-4H-1,3,2-benzodioxaphosphorin-4- one gave the 5′-phosphitylate derivative 3, which on reaction with pyrophosphate gave the 5′-nucleosidylcyclotriphosphite 4. Product 4 was then oxidized with iodine/pyridine/water and deblocked with concentrated ammonium hydroxide to provide the desired 4′-thio-ara-C-5′- triphosphate 5. This triphosphate 5 was converted to 4-thio-ara-C-5′- monophosphate 6 by treatment with snake venom phosphodiesterase I. The details of the synthesis, purification, and characterization of both nucleotides are described. Copyright Taylor & Francis, Inc.