154230-38-3

Upstream product

• 101527-40-6 5'-O-tert-butyldiphenylsilylthymidine 
• 3587-60-8 Benzyloxymethyl chloride 
• 98-88-4 benzoyl chloride 
• 154230-32-7 5'-O-tert-butyldiphenylsilyl-N³-benzyloxymethyl-2'-deoxythymidine 

Downstream Products

• 154230-39-4 (2R,3S,5R)-benzoic acid 5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester 
• 154230-42-9 (2S,3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 154230-43-0 (2R,3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 154230-40-7 (2S,3S,5R)-3-Benzoyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester 
• 154230-41-8 (2S,3S,5R)-3-benzoyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis, anti-HIV activity, and resistance profile of thymidine phosphonomethoxy nucleosides and their bis-isopropyloxymethylcarbonyl (bisPOC) prodrugs

Phosphonomethoxy nucleoside analogs of the thymine containing nucleoside reverse transcriptase inhibitors (NRTIs), 3′-azido-2′,3′-dideoxythymidine (AZT), 2′,3′-didehydro-2′,3′-dideoxythymidine (d4T), and 2′,3′-dideoxythymidine (ddT), were synthesized. The anti-HIV activity against wild-type and several major nucleoside-resistant strains of HIV-1 was evaluated together with the inhibition of wild-type HIV reverse transcriptase (RT). Phosphonomethoxy analog of d4T, 8 (d4TP), demonstrated antiviral activity with an EC50 value of 26 μM, whereas, phosphonomethoxy analogs of ddT, 7 (ddTP), and AZT, 6 (AZTP), were both inactive at concentrations up to 200 μM. Bis-isopropyloxymethylcarbonyl (bisPOC) prodrugs improved the anti-HIV activity of 7 and 8 by >150-fold and 29-fold, respectively, allowing for antiviral resistance to be determined. The K65R RT mutant virus was more resistant to the bisPOC prodrugs of 7 and 8 than bisPOC PMPA (tenofovir DF) 1. However, bisPOC prodrug of 7 demonstrated superior resistance toward the RT virus containing multiple thymidine analog mutations (6TAMs) indicating that new phosphonate nucleoside analogs may be suitable for targeting clinically relevant nucleoside resistant HIV-1 strains.

Synthesis and anti-HIV activity of cyclic pyrimidine phosphonomethoxy nucleosides and their prodrugs: A comparison of phosphonates and corresponding nucleosides

Cyclic phosphonomethoxy pyrimidine nucleosides that are bioisosteres of the monophosphate metabolites of HIV reverse transcriptase (RT) inhibitors AZT, d4T, and ddC have been synthesized. The RT inhibitory activities of the phosphonates were reduced for both dideoxy (dd) and dideoxydidehydro (d4) analogs compared to the nucleosides. Bis-isopropyloxymethylcarbonyl (BisPOC) prodrugs were prepared on selected compounds and provided > 150-fold improvements in antiviral activity. Copyright Taylor & Francis Group, LLC.

Nucleic Acid Mimics. Synthesis of Ethylene Glycol- and Propoxy-Linked Thymidyl-Tetrahydrofuranylthymine Dimers via a Vorbrueggen-Type Glycosylation Reaction

Two thymidyl-tetrahydrofuranylthymine dimers, 15 and 16, were synthesized stereospecifically in good yield via a Vorbrueggen-type reaction between glycol ether 4 or propoxy alcohol 7 and acetate 12.