- STEREOSELECTIVITIES IN THE COUPLING REACTION BETWEEN SILYLATED PYRIMIDINE BASES AND 1-HALO-2,3-DIDEOXYRIBOSE
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Coupling reactions between 1-chloro-2,3-dideoxyribose and silylated pyrimidines have been examined from the point of stereoselectivity.When the reaction was carried out in chloroform, the selectivity was in the anomeric ratio of α:β = 4:6.On the other hand, the presence of tertiary amine raises the selectivity to α:β = 3:7.
- Kawakami, Hiroshi,Ebata, Takashi,Koseki, Koshi,Matsumoto, Katsuya,Matsushita, Hajime,et al.
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p. 2041 - 2054
(2007/10/02)
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- Analogs of pyrimidine nucleosides. 16. Racemic 2′,3′-dideoxynucleosides and their derivatives
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The chlorination of 2-halomethyltetrahydrofurans and acyl derivatives of tetrahydrofuryl alcohol wasstudied; mixtures of 2,5- and 2,2-disubstituted tetrahydrofurans are formed as a result of the reaction. 2,4-Bis(trimethylsilyl) derivatives of uracil, 5-substituted uracils, and cytosine are alkylated by the resulting mixtures of α-chloro ethers without separation, and mixtures of cis and transisomers of 1-(5-substituted-2-tetrahydrofuryl) and 1-(2-substituted-2-tetrahydrofuryl) derivatives of uracil, 5-substituted uracils, and cytosine are obtained. The reaction products were identified onthe basis of their PMR spectra.
- Kaulinya,Liepin'sh,Lidak,Zhuk
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