Studies of Nucleosides and Nucleotides. XXV. Purine Cyclonucleosides. 2. Synthesis of 5'-Deoxyguanosine via an 5', 8-Cyclonucleoside

1 January 1965

journal article
Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN

Vol. 13 (6) , 639-642
https://doi.org/10.1248/cpb.13.639

Abstract

8-Bromoguanosine was directly obtained from guanosine by means of dioxane-bromine bromination. Mesylation of 8-bromoguanosine gave 2', 5'-di-O-mesyl derivative, which was converted to 2'-O-mesyl-8-mercapto-5', 8-anhydroguanosine by the treatment with thiourea. Desulfurization of 5', 8-cyclonucleoside and subsequent removal of mesyl group gave 5'-deoxyguanosine. Acid hydrolysis of 2'-O-mesyl-5'-deoxyguanosine gave 2'-O-mesyl-5'-deoxyribose.

Keywords

THIOUREA
MESYLATION
CYCLONUCLEOSIDES
CONVERTED
TREATMENT
DIRECTLY
PURINE
XXV

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