151201-01-3

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 73108-51-7 5'-deoxy-2',3'-isopropylidene-5',5'-[(N,N'-diphenyl)ethylenediamino]uridine 

Downstream Products

• 151201-02-4 5'-deoxy-5',5'-difluoro-2',3'-O-isopropylidene-N⁽³⁾-(4-methoxybenzyl)-uridine 
• 121845-98-5 (3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde 

Relevant academic research and scientific papers

Some novel nucleoside rearrangements effected by (diethylamino)sulphur trifluoride: synthesis and antiviral properties of some fluorine-containing 3'-azido-3'-deoxythymidine derivatives

The reaction of pyrimidine nucleoside 5'-aldehydes with (diethylamino)sulphur trifluoride (DAST) to produce 5'-deoxy-5',5'-difluoronucleosides is reported.The preferred reaction is the production of the O2,5'-anhydro-5'-fluoronucleoside.If this is prevented by substitution at O4 or N-3 then, in the former case, either DAST no longer reacts or under drastic conditions the C(1')-N(1) bond breaks and the heterocyclic base remains joined by C-5' O2 to a glycosyl fluoride.In the latter case, the 5'-aldehyde of 2',3'-O-isopropylideneneuridine gives the 5'-deoxy-5',5'-difluoro compound as the sole identifiable product.With the 5'-aldehyde of AZT as starting material, treatment with DAST yields a diastereoisomeric mixture of glycosyl fluorides and a derivative of 5'-deoxy-5',5'-difluoro AZT from which 3'-azido-3',5'-dideoxy-5',5'-difluorothymidine could be isolated.This compound is not toxic nor has it any activity against human immunodeficiency virus type-1 (HIV-1) at concentrations up to 100 μM.