title: Modular Synthesis of Constrained Ethyl (cEt) Purine and Pyrimidine Nucleosides.
abstract: A modular and scalable approach to pyrimidine- and purine-containing constrained ethyl (cEt) nucleosides is demonstrated. Minimizing stereochemical adjustments and protecting group manipulations, diacetone glucose is converted to two representative cEt nucleosides via a functionalized, common intermediate. The retrosynthetic approach to this complex class of drug precursors offers clear benefits over existing routes based on step count and efficiency.
authors.affiliation: Pharmaceutical Development, AstraZeneca, Charter Way, Macclesfield SK10 2NA, United Kingdom.
authors.forename: Helen
authors.initials: H
authors.lastname: Blade
authors.affiliation: Pharmaceutical Development, AstraZeneca, Charter Way, Macclesfield SK10 2NA, United Kingdom.
authors.forename: Derek
authors.initials: D
authors.lastname: Bradley
authors.affiliation: Pharmaceutical Development, AstraZeneca, Charter Way, Macclesfield SK10 2NA, United Kingdom.
authors.forename: Louis
authors.initials: L
authors.lastname: Diorazio
authors.affiliation: Pharmaceutical Development, AstraZeneca, Charter Way, Macclesfield SK10 2NA, United Kingdom.
authors.forename: Timothy
authors.initials: T
authors.lastname: Evans
authors.affiliation: Pharmaceutical Development, AstraZeneca, Charter Way, Macclesfield SK10 2NA, United Kingdom.
authors.forename: Barry R
authors.initials: BR
authors.lastname: Hayter
authors.affiliation: Pharmaceutical Development, AstraZeneca, Charter Way, Macclesfield SK10 2NA, United Kingdom.
authors.forename: Gareth P
authors.initials: GP
authors.lastname: Howell
mesh_terms: D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009705:Nucleosides; D011355:Prodrugs; D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides