Stereoselective synthesis of 4'-carbon-substituted xylofuranosyladenines | Zendy

Yutaka Kubota | Zendy

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Stereoselective synthesis of 4'-carbon-substituted xylofuranosyladenines

Author(s) -

Yutaka Kubota

Publication year - 2004

Publication title -

nucleic acids symposium series

Language(s) - Uncategorized

Resource type - Journals

eISSN - 1746-8272

pISSN - 0261-3166

DOI - 10.1093/nass/48.1.47

Subject(s) - stereoselectivity , epoxide , dimethyldioxirane , chemistry , reagent , silylation , ring (chemistry) , stereochemistry , organic chemistry , catalysis

Epoxidation of 2',5'-bis-O-silyl-protected N6-pivaloyl-3',4'-unsaturated adenine nucleosides (1, 2 and 3) with dimethyldioxirane uniformly proceeded face-selectively to give the respective 3',4'-beta-epoxides (4, 5 and 6). Ring cleavage of these epoxides examined with Me3Al in CH2Cl2 showed that the TBDMS (4) or TES (5) protected epoxide gave the desired 4'-alpha-methylated product (8 or 10) as the major stereoisomer, while use of the TBDPS protected epoxide (6) resulted in reverse stereoselectivity. Reactions of 4 with other organoaluminum reagents were also carried out.

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