19200-56-7

Upstream product

• 1374011-57-0 1'-(adenin-9-yl)-3'-deoxy-5'-O-benzyl-β-D-apio-D-furanose 
• 1374011-55-8 1,2-di-O-acetyl-3-deoxy-5-(O-benzyl)-D-apio-D-furanose 
• 287933-91-9 (3R)-3-(((4-methoxyphenyl)-diphenylmethoxy)-methyl)-2,3-dihydrofuran 
• 287933-70-4 (3S)-4-phenylsulfonyl-2,3-dihydrofuran-3-methanol 
• 287933-69-1 (S)-2-((E)-2-Benzenesulfonyl-vinyloxymethyl)-oxirane 
• 18055-47-5 N-Benzoyl-N,9-bis(trimethylsilyl)adenin 
• 287933-80-6 6-N-benzoyl-9-((1R,2R,3S)-tetrahydro-2-acetoxy-3-(((4-methoxyphenyl)-diphenylmethoxy)-methyl)-1-furanyl)-9H-adenine 
• 4005-49-6 N-benzoyladenine 
• 448896-47-7 9-((1R,2R,3S)-tetrahydro-2-hydroxy-3-(((4-methoxyphenyl)-diphenylmethoxy)-methyl)-1-furanyl)-9H-adenine 
• 287933-90-8 (3R)-3-(((4-methoxyphenyl)-diphenylmethoxy)-methyl)-4-phenylsulfonyl-2,3-dihydrofuran 

Downstream Products

• 1610460-02-0 1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(benzoxy-L-alaninyl)]phosphate 
• 1610460-04-2 1'-(adenin-9-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate 

Relevant academic research and scientific papers

Synthesis of an apionucleoside family and discovery of a prodrug with anti-HIV activity

We report the synthesis of a family of d- and l-furano-d-apionucleosides, their 3'-deoxy, as well as their 2',3'-dideoxy analogues with thymine and adenine nucleobases. Single carbon homologation of 1,2-O-isopropylidene-d- glycero-tetrafuranos-3-ulose (15) and optimized glycosylation conditions involving microwave irradiation were key to the successful synthesis of the target compounds. While all target nucleosides failed to show significant antiviral activity, we demonstrated that the triphosphate of 2',3'-deoxy-d-apio-d-furanoadenosine (1), in contrast to that of its d-apio-l-furanose epimer 2, was readily incorporated into a DNA template by HIV reverse transcriptase to act as a DNA chain terminator. This led us to convert adenine derivative 1 into two phosphoramidate prodrugs. ProTide 9b was found active against HIV-1 and HIV-2 (EC50 = 0.5-1.5 μM), indicating that the lack of activity of the parent nucleoside, and possibly also other members of the d-apio-d-furanose nucleoside family must be sought in the inefficient cellular conversion to the monophosphate.

Synthesis and biological activity of a series of methylene-expanded oxetanocin nucleoside analogues

A series of methylene-expanded oxetanocin nucleoside analogues, e.g. analogues of 2 and the known antiviral nucleosides AZT, FLT, and ddC (3) were prepared by a very direct route beginning with the readily available (S)-glycidol 4 and proceeding via the dihydrofuran-3-methanols 9a,b. Biological testing of these modified nucleosides indicates that they are non-cytotoxic compounds with generally weak antiviral activity. However, the guanosine analogue 2G showed pronounced activity vs. herpes simplex virus type 1 (HSV-1) in cell culture and was HSV-1-encoded thymidine kinase dependent. This compound is therefore an interesting new lead structure for the development of new anti-HSV agents.

Efficient synthesis of several methylene-expanded oxetanocin nucleoside analogues

S-Glycidol 4 has been converted by a direct route via the dihydrofuran- 3-methanols 9ab into a series of methylene-expanded oxetanocin nucleoside analogues, e.g., analogues of the normal nucleosides 2 and the known antiviral nucleosides, AZT, FdT, and ddC, 3. (C) 2000 Elsevier Science Ltd.