A New Synthetic Route towards the Mono-O-protected Anti-conformationally Constrained Pyrimidine Acyclic Nucleoside

• Published in: Chemical & pharmaceutical bulletin Vol. 50; no. 8; pp. 1028 - 1030
• Main Authors: Liu, Chi-Tsan, Tu, Tsu-Chiang, Hsu, Ling-Yih
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.08.2002; Pharmaceutical Soc Japan; Maruzen; Japan Science and Technology Agency
• Subjects: Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Exact sciences and technology; Hydrocarbons, Acyclic - chemical synthesis; Hydrocarbons, Acyclic - chemistry; Life Sciences & Biomedicine; new synthetic route; Nucleic Acid Conformation; Nucleosides, nucleotides and oligonucleotides; oligonucleotide; Oligonucleotides - chemical synthesis; Oligonucleotides - chemistry; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; pyrimidine acyclic nucleoside; Pyrimidine Nucleosides - chemical synthesis; Pyrimidine Nucleosides - chemistry; Science & Technology; ETHERS; new synthetic route; pyrimidine acyclic nucleoside; oligonucleotide; OLIGONUCLEOTIDES; Molecular rigidity; Acyclic nucleoside; Ether; Hydroxylation; Dealkylation; Benzyl alcohol; Alkylation; Primary alcohol; Cyclization; Bicyclic compound; Chemical synthesis; Pyrimidine nucleoside; Oxygen nitrogen heterocycle
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.50.1028

Novel synthetic approach to mono-O-protected anti-conformationally constrained pyrimidine acyclic nucleoside was attained from the coupling of lithiated 2,4-dimethoxy-6-methylpyrimidine with 1-benzyloxy-3-(tert-butyldiphenylsilyloxy)propan-2-one, followed by the sequential reactions of methylthiomethylation, cyclization, hydroxylation, and dealkylation.