24649-69-2

Upstream product

• 4060-34-8 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride 
• 700-49-2 2-fluoroadenine 
• 52522-49-3 2,3,5-tri-O-benzyl-1-(4-nitrobenzoyloxy)-D-arabinofuranose 
• 143482-59-1 6-azido-2-fluoro-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine 
• 24880-52-2 2,6-diamino-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine 
• 3257-73-6 9-(2',3',5'-tri-O-benzyl-β-D-arabinofuranosyl)adenine 

Downstream Products

• 146-78-1 Fludarabine 

Relevant academic research and scientific papers

Preparation of a fludarabine intermediate via selective alkylation of 2-fluoroadenine

The reaction between 2-fluoroadenine ( 3 ) and 1,3,5-tri- O -benzyl-1- α -d-chloroarabinofuranose ( 4 ) with potassium t- amylate was evaluated in various solvents to afford 9- β -d-(2,3,5-tri- O -benzyl- arabinofuranosyl)-2-fluoroadenine ( 5 ) and the co

Hydrogenation of 2-fluoro-9-(2,3,5-tri-o-benzyl-beta-D-arabinofuranosyl)adenine

A process for the preparation of 2-fluoro-9-beta-D-arabinofuranosyl purine (VII) by a reaction of palladium chloride and hydrochloric acid with 2-fluoro-9-(2,3,5-tribenzyl-beta-D-arabinofuranosyl)adenine (VI) at elevated pressures in a solvent for (VI) is described. The reaction is rapid, economical and efficient.

6-azido-2-fluoropurine, useful in the synthesis of nucleosides

This invention pertains to novel methods of synthesizing fludarabine, fludarabine phosphate and related nucleoside pharmacologic agents utilizing 6-azido-2-fluoropurine as a novel intermediate. In particular this invention pertains to a synthesis of fludarabine where the relatively low yield fluorination step is done before the costly coupling step.

Process for the preparation of 2-amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl) adenine and novel intermediates

A process for the preparation of 2,6-diamino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine (V) by reacting 2,6-di(alkoxyacetamido)purine (II) with 2,3,5-tri-O-benzyl-1-chloro-alpha-D-arabinofuranose (III) to produce 2,6-di(alkoxyacetamido)-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine (IV) and then deprotecting the 2,6-positions to produce the 2,6-diamine (V) is described. The process provides purine (V) in high yield. Purine (V) is an intermediate in the preparation of 9-beta-D-arabinofuranosyl-2-fluoroadenine which is a cytotoxic agent.

Anticancer and antiviral activity of 9-β-D-arabinofuranosyl-2-fluoroadenine

A method of utilizing 9-β-D-arabinofuranosyl-2-fluoroadenine, known as 2-F-AraA (NSC 118218), in the treatment of murine leukemia and as an antiviral agent for DNA viruses, such as DNA viruses Herpes Simplex Virus Type I and Vaccinia virus grown in H.Ep-2 cells in culture. An operable dosage for utilization of 2-F-AraA is a treatment span of 1-10 days with the dosage 2-8 times per day at 8-400 mg/kg/dose. It has been further found that a single dosage on days 1, 5, and 9 based on a 10-day treatment schedule gave satisfactory results.

Procedure for the preparation of 9-β-D-arabinofuranosyl-2-fluoroadenine

The present invention is an improved multi-step process for the production of 9-β-D-arabinofuranosyl-2-fluoroadenine (2-F-AraA) and an improvement over the process of Montgomery and Hewson, J. Med. Chem., 12:498 (1969). This compound is an important tool in antitumor therapy and has shown activity against leukemia L1210 and P388 in animals as well as being a potent antiviral agent. Its therapeutic effectiveness occurs because 2-F-AraA is not a substrate for adenosine deaminase which vitiated against the activity of the parent compound 9-β-D-arabinofuranosyladenine (araA) as indicated in experimental animal cancers.An advantage of making 2-F-AraA by the present process is that there is a sharply increased yield based on the chlorosugar up to about 400 percent. In the present improved process the differences lie in utilizing as a reactant 2,4,5,6-tetraaminopyrimidine; the acetylation of 2-aminoadenine in acetic acid and pyridine; the reaction of 2,6-diacetamidopurine with chlorosugar in ethylene chloride in the presence of a molecular sieve and subsequent deacetylation with methanolic sodium methoxide. Further, the diazotization step is carried out in a homogenous mixture of tetrahydrofuran and fluoboric acids. Finally, the O-benzyl groups are removed by the use of boron trichloride in ether.