Synthesis of 1-(3-deoxy-3-halo-β-D-arabinofuranosyl)-6-azauracil, 1-(3-deoxy-β-D-threo-pentofuranosyl)-6-azauracil, and their acetyl derivatives

Brokeš, J.; Beránek, J.

doi:10.1135/cccc19753071

Cited by 5 publications

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“…18 (to3HX 0H CH3 CH CH ' 7.0 Hz), 4.63 (q. 2Hg -0-CH CH 6 (t. 3H~2-L3-CH CHH -'23 3.68 (m, 2H, H5'), 4.70 (m, 1H, H4'), 5.26 (s, 1H, H1', 3H H' = 0.7 Hz), 5.67 (d H, H =5.0 Hz), 5.88 (dd, 1H H3' H3,,H4 = 6.0 Hz), 7.25-7,65, 7.80-8.15 (m, 1SH, arom. protons).…”

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Acetylation and cleavage of purine nucleosides. Synthesis of 6-azauridine, 5-fluorouridine, and 5-methyluridine.

Beránek

Hřebabecký

1976

Nucleic Acids Research

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Inosine (I) when acetylated with acetic anhydride in the presence of acetyl chloride in acetic acid solution (the so called "acid acetylation"), affords an acetylated nucleoside III (75%) along with cleavage products of the nucleoside (hypoxanthine, 19%). The reaction of I with acetyl chloride (7 days) results in the formation of hypoxanthine (95%) and triacetylribofuranosyl chloride (IV) isolated in the form of tetraacetylribofuranose (47%). The acetylated purine nucleoside affords a similar result by reaction with acetyl chloride or acetyl bromide. 2'-Deoxyuridine gives a diacetyl derivative (80%) by reaction with acetyl bromide. On treatment with acetyl bromide, the nucleoside bond of purine nucleosides is quantitatively cleavaged (4 h, 20 degrees C) with the formation of tri-O-acetyl-D-ribofuranosyl bromide (X). The halogenose X affords pure beta-anomers, namely, 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose (75%), the triacetyl derivatives of 5-methyluridine (XVIIa; 75%, referred to guanosine), 6-azauridine (XVIII; 71%), and 5-fluorouridine (XIXa; 75%).

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confidence: 99%

Acetylation and cleavage of purine nucleosides. Synthesis of 6-azauridine, 5-fluorouridine, and 5-methyluridine.

Beránek

Hřebabecký

1976

Nucleic Acids Research

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ChemInform Abstract: ANALOGUES OF NUCLEOSIDES PART 5, SYNTHESIS OF 1‐(3‐DEOXY‐3‐HALO‐BETA‐D‐ARABINOFURANOSYL)‐6‐AZAURACIL, 1‐(3‐DEOXY‐BETA‐D‐THREO‐PENTOFURANOSYL)‐6‐AZA‐URACIL AND THEIR ACETYL DERIVATIVES

Brokeš¹,

Beránek²

1975

Chemischer Informationsdienst

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Chemical Transformations of the Sugar Moiety of Nucleosides

Moffatt¹

1979

Nucleoside Analogues

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The last two decades have witnessed the proliferation of a rather vast literature concerning the synthesis and biological properties of nucleoside analogues. These interesting compounds can be roughly subdivided into two major groups--those containing modified heterocyclic bases, and those in which the sugar moiety has been altered and is no longer ribose or 2-deoxyribose as found in nucleic acids. Base analogues have in general been prepared either via N-glycosidation of suitably modified heterocycles or by structural transformations of the base moiety in existing nucleosides. Both of these approaches will be considered in detail during this meeting by my colleagues Drs. VorbrUggen, Robins and Townsend. In a related way, nucleosides containing modified carbohydrate moieties have frequently been prepared via glycosidation of an appropriate purine or pyrimidine base with a suitable derivative of the desired sugar. Alternatively, a great deal of effort has been devoted to the development of specific chemical transformations suitable for introducing the desired modifications into the sugar moiety of intact nucleosides. It is this latter approach that has particularly fascinated the group in our laboratory and that I wish to review for you today. The subject is, however, a rather vast one, encompassing an enormous number of references, and accordingly I must, of necessity, be somewhat selective in what I specifically mention. Accordingly, I have decided to restrict my attentions to analogues of pentofuranosyl nucleosides and to make almost no mention of hexose derivatives tContribution No. 527 from the Institute

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Synthesis of 1-(3-deoxy-3-halo-β-D-arabinofuranosyl)-6-azauracil, 1-(3-deoxy-β-D-threo-pentofuranosyl)-6-azauracil, and their acetyl derivatives

Cited by 5 publications

References 0 publications

Acetylation and cleavage of purine nucleosides. Synthesis of 6-azauridine, 5-fluorouridine, and 5-methyluridine.

Acetylation and cleavage of purine nucleosides. Synthesis of 6-azauridine, 5-fluorouridine, and 5-methyluridine.

ChemInform Abstract: ANALOGUES OF NUCLEOSIDES PART 5, SYNTHESIS OF 1‐(3‐DEOXY‐3‐HALO‐BETA‐D‐ARABINOFURANOSYL)‐6‐AZAURACIL, 1‐(3‐DEOXY‐BETA‐D‐THREO‐PENTOFURANOSYL)‐6‐AZA‐URACIL AND THEIR ACETYL DERIVATIVES

Chemical Transformations of the Sugar Moiety of Nucleosides

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