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- W2952114966 abstract "The synthesis of 8-aza-2′-deoxyadenosine ( = 7-amino-3H-1,2,3 triazolo[4,5-d]pyrimidine N3-(2′-deoxy-β-D-ribofuranoside); 1) as well as the N2- and N1-(2′-deoxy-β-D-ribofuranosides) 2 and 3 is described. Glycosylation of the anion of 7-amino-3H-1,2,3-triazolo[4,5-d]pyrimidine (6) in DMF yielded three regioisomeric protected 2′-deoxy-β-D-ribofuranosides, i.e. the N3-, N2-, and N4-glycosylated isomers 7 (14%), 9 (11%), and 11 (3%), respectively, together with nearly equal amounts of their α-D-anomers 8 (13%), 10 (12%), and 12 (4%; Scheme 1). The reaction became Stereoselective for the β-D-nucleosides if the anion of 7-methoxy-3H-1,2,3-triazolo[4,5-d]pyrimidine (13) was glycosylated in MeCN: only the N3-, N2, and N1-(2′-deoxy-β-D-nucleosides) 14 (29%), 15 (32%), and 16 (23%), respectively, were formed (Scheme 2). NH3 Treatment of the methoxynucleosides 14–16 afforded the aminonucleosides 1–3. The anomeric configuration as well as the position of glycosylation were determined by combination of 13C-NMR, 1H-NMR, and 1D-NOE difference spectroscopy. Compound 1 proved to be a substrate for adenosine deaminase, whereas the regioisomers 2 and 3 were not deaminated." @default.
- W2952114966 created "2019-06-27" @default.
- W2952114966 creator A5060754316 @default.
- W2952114966 creator A5060869360 @default.
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- W2952114966 date "1990-02-06" @default.
- W2952114966 modified "2023-09-27" @default.
- W2952114966 title "ChemInform Abstract: Synthesis of 8-Aza-2′-deoxyadenosine and Related 7-Amino-3H-1,2,3-triazolo(4,5-d)pyrimidine 2′-Deoxyribofuranosides: Stereoselective Glycosylation via the Nucleobase Anion." @default.
- W2952114966 cites W2021861488 @default.
- W2952114966 doi "https://doi.org/10.1002/chin.199006307" @default.
- W2952114966 hasPublicationYear "1990" @default.
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