Synthesis of 1,1,2-trisubstituted cyclopropane nucleosides in enantiomerically pure forms

• Published in: Nucleosides, nucleotides & nucleic acids Vol. 38; no. 12; pp. 921 - 941
• Main Authors: Fushihara, Daichi, Fukuda, Hayato, Abe, Hiroshi, Shuto, Satoshi
• Format: Journal Article
• Language: English
• Published: PHILADELPHIA Taylor & Francis 02.12.2019; Taylor & Francis Ltd
• Subjects: Antiviral agents; Antiviral Agents - chemical synthesis; Biochemistry & Molecular Biology; carbocyclic nucleoside; Chemotherapy; Cyclization; Cyclopropane nucleoside; Cyclopropanes - chemical synthesis; Drug Design; Intermediates; Lactones; Life Sciences & Biomedicine; Molecular Structure; Nucleosides; Nucleosides - chemical synthesis; Oligonucleotides; Oxidation-Reduction; Ribose; Science & Technology; Stereoisomerism; Structure-Activity Relationship; Cyclopropane nucleoside; LOWER METHYLENE HOMOLOG; POTENT; CARBOCYCLIC OXETANOCIN; carbocyclic nucleoside; ENANTIOSELECTIVE SYNTHESIS; STEREOCHEMICAL DIVERSITY; CONFORMATIONALLY RESTRICTED ANALOGS; ANTIVIRAL ACTIVITY; NEPLANOCIN ANALOGS; RECEPTOR; DERIVATIVES
• ISSN: 1525-7770; 1532-2335
• DOI: 10.1080/15257770.2019.1625380

Due to the unique rigid and small steric feature of cyclopropane, cyclopropane nucleosides (CPNs) in which the ribose (deoxyribose) of nucleosides are replaced by a hydroxy-substituted cyclopropane, are of great biological interest. Novel 1,1,2-trisubstituted cyclopropane nucleosides were synthesized in enantiomerically pure forms as potential antiviral agents. In the synthesis, two cyclopropane tosylates, which were prepared from chiral cyclopropane lactones previously reported by us, were used effectively as common intermediates for the CPNs. These CPNs are also potentially useful as nucleoside units to incorporate into oligonucleotides in nucleic acids chemotherapy studies.