Stereospecific syntheses of 1-[2,3-dideoxy-3-(N-hydroxy-N-methylamino)-α-D-and α-L-erythro-pentofuranosyl]thymine from L-and D-glutamic acids respectively

Article Article scientifique Article Stereospecific syntheses of 1-[2,3-dideoxy-3-(N-hydroxy-N-methylamino)-α-D-and α-L-erythro-pentofuranosyl]thymine from L-and D-glutamic acids respectively eng 1996 author Tronchet Jean Marcel Julien 25054 author Criton Marc 26716 author Zsely Schaffter Martina Maria 24230 author Besomi Pascal Gilbert 44896 author Barbalat Françoise 25461 205-212 1029-2438 Conjugate addition of N-methylhydroxylamine upon (S)-4-(tert-butyldimethylsilyloxymethyl)butenolide 5 proceeded stereospecifically to afford the D-erythro isomer 6. A stereospecific phenylselenylation α to the carbonyl group led to the D-arabino isomer 12, allowing the stereoselective synthesis from L-glutamic acid of the α-D isomer 16 of the title compounds. Conversely, the α-L isomer 16' was obtained from D-glutamic acid. Upon skipping the orientating phenyselenylation step, both α-D-erythro (16) and β-D-erythro (18) isomers were obtained. Contrasting with the significant anti-HIV activity of the β-D-threo isomer, the β-D-erythro nucleoside exhibited no such property but did exhibit anti-VZV activity. On the other hand, the α-D-erythro isomer (16) was devoid of any tested (HIV, HSV, VZV, CMV) antiviral activity and the α-L-isomer 16' was inactive against HIV. Nucleosides Hydroxyamino Spin labelling Antiviral activity Dewey 615 31 Section des sciences pharmaceutiques 17 false Carbohydrate letters 2 42dcfdad-69b2-4a22-b8b1-946ae3c0755e Article (Published version) Restricted Tronchet_CL_199602205.pdf 3065996 application/pdf restrictedAccess Faculté des sciences / Section des sciences pharmaceutiques

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Stereospecific syntheses of 1-[2,3-dideoxy-3-(N-hydroxy-N-methylamino)-α-D-and α-L-erythro-pentofuranosyl]thymine from L-and D-glutamic acids respectively	Carbohydrate letters			1996	140	0

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Besomi, Pascal Gilbert