191802-82-1

Upstream product

• 64904-47-8 2-benzoyloxyacetaldehyde 
• 59237-80-8 1-(2-hydroxy-1-hydroxymethyl-ethyl)-1H-pyrimidine-2,4-dione 
• 210760-38-6 3-Benzoyl-1-(2-trityloxy-1-trityloxymethyl-ethyl)-1H-pyrimidine-2,4-dione 
• 59237-83-1 N-1-(bistrityloxymethyl)methyluracil 

Downstream Products

• 191802-84-3 N-1-[(2-benzoyloxymethyl)-1,3-dioxan-5-yl]thiouracil 
• 1027832-07-0 Benzoic acid 5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-[1,3]dioxan-2-ylmethyl ester 

Relevant academic research and scientific papers

Ring-expanded nucleoside analogues. 1,3-Dioxan-5-yl pyrimidines

1,3-Dioxan-5-yl pyrimidine nucleoside analogues, higher homologues of antiviral and anticancer 1,3-dioxolanes, were prepared from bis-1,3- tritylglycerol and 3-benzoylated bases (uracil, 5-fluorouracil, thymine). Mitsunobu condensation, deprotection, and cycloacetalization gave cis/trans mixtures of 2,5-disubstituted-1,3-dioxanes in which the desired cis stereoisomers predominated. Cytosine derivatives could not be obtained in this manner; N4-benzoylcytosine afforded an O-2 alkylated Mitsunobu product that rearranged to an O2-(2,3-dihydroxypropyl)cytosine on detritylation with aqueous acetic acid. Cytosine and 5-fluorocytosine nucleosides were therefore prepared from the corresponding uracils via their 1,2-4-triazole derivatives. 1H NMR data established the conformational preference for equatorial 2'- hydroxymethyl and axial 5'-base in the cis isomers; the trans compounds were diequatorial. Despite their conformations, the cis nucleosides showed no antiviral activity.

Synthesis of sk-membered nucleoside analogs. Part 1: Pyrimidine nucleosides based on the 1,3-dioxane ring system

The synthesis of pyrimidine nucleosides, cis-N-l-[(2-hydroxymethyl)-1,3-dioxan-5-yl]uracil (4) cfs-AM-[(2-hydroxymethyl)-1,3-dioxan-5-yl]thymine (5) and cis-Nl-[(2-hydroxymethyl)-1,3-dioxan-5-yl]cytosine (6) and their corresponding trans isomers is descri