Stereospecific synthesis of alpha-anomeric pyrimidine nucleoside.
A facile stereospecific synthetic method for alpha-anomeric 2'-deoxypyrimidine nucleoside unit utilizing aminooxazoline derivative of ribofuranose was investigated. Thus, easily accessible riboaminooxazoline derivative prepared by ribose and cyanamid was allowed to react with ethyl alpha-bromoethylacrylate to give corresponding adduct. The adduct was cyclized by strong base such as potassium t-butokiside. The resulted 2,2'-cyclonucleoside was then treated with acetyl bromide followed by n-butyltin hydride to give alpha-anomeric 3',5'-di-O-acetylthymidine. 3',5'-Di-O-acety groups of the nucleoside were easily removed by the action of excess of triethyl amine in methanol. Essentially same procedure afforded corresponding 2'-deoxyuridine, which was further, converted to alpha-anomeric 2'-deoxycytidine.
Shinozuka
K
K
Faculty of Engineering, Gunma University, 1-5-1 Tenjincho, Kiryu, Gunma 376-8515, Japan.
Matsumoto
N
N
Nakamura
A
A
Hayashi
H
H
Sawai
H
H
D003841:Deoxycytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D003853:Deoxyribonucleosides / Q000138:chemical synthesis / Q000737:chemistry; D003857:Deoxyuridine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D003853:Deoxyribonucleosides; D011741:Pyrimidine Nucleosides; D003841:Deoxycytidine; D003857:Deoxyuridine