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• W1997620468 abstract "Addition of methyl nitroacetate to 1,2:5,6-di-O-isopropylidene-α-d-ribo-hexofuranos-3-ulose in the presence of ammonium acetate in anhydrous N,N-dimethylformamide afforded 1,2:5,6-di-O-isopropylidene-3-C-(R,S)nitro(methoxy-carbonyl)methyl-α-d-allofuranose (2). Reduction of the nitro acetate 3 over palladium-on-charcoal gave the oxime 4, whereas reduction of 3 over Raney nickel afforded methyl l (and d)-2-(3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-d-allofuranos-3-yl)-glycinates (5 and 6), in 67 and 8% yields, respectively. Saponification of 5 and 6 afforded the glycos-3-yl-α-amino acids 11 and 12. Conversion of the allofuranos-3-yl adduct 2 into the glucofuranos-3-yl reduction-products 13 and 14 was achieved by treatment of 2 with methanol and acetic anhydride in the presence of palladium-on-charcoal. The N-trifluoracetyl derivative (10) of 5, underwent selective hydrolysis by 66% acetic acid to afford a diol that was acetylated to afford the allo tri-acetate 15. The 5,6-glycol was selectively degraded by standard reactions to yield methyl N-acetyl-l-2-(5-O-acetyl-1,2-O-isopropylidene-α-d-ribofuranos-3-yl)glycinate (19). Application of the triflate-alkylation synthesis of nucleosides to the allo trifluoroacetyl amino acid 15 and silylated thymine yielded 1-[2,3,5,6-tetra-O-acetyl-[3-C-(methyl N-trifluoroacetyl-l-2-glycinate)]-β-d-allofuranosyl]thymine (23) in 93% yield. Deprotection of 23 to yield the nucleoside amino acid 25 was not successful." @default.
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• W1997620468 date "1980-02-01" @default.
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• W1997620468 title "Synthesis of an analog of the nucleoside moiety of the polyoxins" @default.
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• W1997620468 doi "https://doi.org/10.1016/s0008-6215(00)85132-0" @default.
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