Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
Studies on Chemotherapeutic Agents.II. A Synthesis of Purine Nucleosides of D-Glucuronic Acid
Torahiko KishikawaHidetaka Yuki
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Volume 14 (1966) Issue 12 Pages 1360-1364

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Abstract

Condensation of 4-ethylthio-5-nitro-6-chloropyrimidine with methyl 1-amino-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate was effectd to give methyl 1-deoxy-1-(4-ethylthio-5-nitro-6-pyrimidinylamino)-2, 3-4-tri-O-acetyl-D-glucopyranuronate (VI). Hydrogenation of nitro group of VI in the presence of platinum-catalyst and subsequent ring closure of 4, 5-diamino-derivative (VII) with carbon disulfide were achieved. 6-Ethylthio group of X was replaced to 6-hydrazino group followed by treatment with Raney nickel to afford 1-deoxy-1-(6-amino-9-purinyl)-β-D-glucopyranuronamide (XII). VII was reacted with sodium nitrite to give ν-triazolo derivative (XIII), 6-ethylthio group of which was readily aminated to yield 1-deoxy-1-(7-amino-3H-ν-triazolo [4, 5-d] pyrimidin-3-yl)-β-D-glucopyranuronamide (XIV).

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