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Abstract

(1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol (1) was converted to (3aS,4R,5S,7aR)-4-(benzyloxy)-2-oxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-ol (3) and subsequently to (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-yl benzoate (4). Treatment of sulfate 4 with adenine and DBU afforded, after deprotection, 7 and 22 in low yields. Reaction of sulfite 3 with lithium azide gave (1R,2R,3S,6S)-6-azido-2-(benzyloxy)-4,4-bis[(trityloxy)methyl]-cyclohexane-1,3-diol (10) and (1S,4R,5S,6S)-5-azido-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]-cyclohexane-1,4-diol (11) which were, after separation, reduced with LAH to (1R,2R,3S,6S)-6-amino-2-(benzyloxy)-4,4-bis[(trityloxy)methyl]cyclohexane-1,3-diol (9) and (1S,4R,5S,6S)-5-amino-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexane-1,4-diol (12). Amino derivatives 9 and 12 were transformed to (1R,2R,3S,6S)-6-(6-amino-9H-purin-9-yl)-4,4-bis(hydroxymethyl)cyclohexane-1,2,3-triol (7), (1R,2R,3S,6S)-6-[6-(cyclopropylamino)-9H-purin-9-yl]-4,4- bis(hydroxymethyl)cyclohexane-1,2,3-triol (16), (1S,2S,3S,4R)-3-[6-(cyclopropylamino)-9H-purin-9-yl]-6,6-bis(hydroxymethyl)cyclohexane-1,2,4-triol (20), (1S,2S,3S,4R)-3-(6-amino-9H-purin-9-yl)-6,6-bis(hydroxymethyl)cyclohexane-1,2,4-triol (22), and 2-amino-9-[(1S,2R,3R,4S)- 2,3,4-trihydroxy-5,5-bis(hydroxymethyl)cyclohexyl]-9H-purin-6(1H)-one (27).

Keywords: Carbasugars; Carbocyclic hexopyranoses; Cyclohexanes; Azides; Nucleosides; Carbocyclic nucleosides; Purines; 6-(Cyclopropylamino)purine; Adenine; Guanine.

References: 30 live references.