2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → cis-N-[2-[(2-benzothiazolyl)thio]cyclopentyl]-2-chloroadenosine

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Reaction Steps

The above cis-2-(2-benzothiazolyl)cyclopentylamine hydrochloride (1.5 g, 4.6 mmol) was combined with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 4.5 mmol) and triethylamine (2.49 ml) and reacted by the method described in Example 1. Deacylation of the purified cis-2',3',5'-tri-O-acetyl-N-[2-[(2-benzothiazolyl)thio ]cyclopentyl]-2-chloroadenosine using sodium methoxide in methanol provided the title cis-N-[2-[(2-benzothiazolyl)thio]cyclopentyl]-2-chloroadenosine (0.89 g, 38%) as a foam (following column chromatography) (a ca. 2:1 mixture of diastereoisomers), 1H NMR (DMSO-d6) δ 1.62-2.45 (6H, 5m, --CH2CH2CH2 --), 3.52-3.60 (1H, m, H-5'a), 3.64-3.70 (1H, m, H-5'b), 3.94 (1H, br q, H-4'), 4.11 (1H, br q, H-3'), 4.62 (1H, q, H-2'), 5.75-5.83 (1H, 2m, H-1'), 7.26-7.94 (4H, 4m, Ar-H).

Provenance & Evidence