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Stereoselective syntheses of heptaprenylphosphoryl β-d-arabino-and β-d-ribo-furanoses

✍ Scribed by Avraham Liav; Ewa Ciepichal; Ewa Swiezewska; Adela Bobovská; Petronela Dianišková; Jaroslav Blaško; Katarína Mikušová; Patrick J. Brennan

Book ID
104096368
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
259 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

The stereoselective syntheses of heptaprenylphosphoryl b-D-arabinofuranose and heptaprenylphosphoryl b-D-ribofuranose are described. In the synthesis of the D-arabino product, the stereoselectivity was achieved by the coupling of a suitably protected b-D-arabinofuranosyl phosphate intermediate with an activated form of heptaprenol and subsequent deprotection. In the case of the ribo-analog, the desired b-anomer could be obtained by the more convenient phosphoramidite method. The products were successfully employed in the mycobacterial epimerase assay.

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✍ Masaharu Iwakawa; Olivier R. Martin; Walter A. Szarek 📂 Article 📅 1983 🏛 Elsevier Science 🌐 English ⚖ 568 KB

l-(5-Deoxy-P-D-arabinn-hexofutanoayl)cytosine (4'-homoara-C) (ll), a higher homolog of the antileukemic agent ara-C (1-B-D-arabinofuranosylcytosine), was prepared by two independent routes. The first one involved the inversion of configuration at C-2' of the D-rib0 epimer (1-(S-dzoxy-P-D-ribo-hexofu