2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → N-[(R)-1-(2-benzothiazolyl)thio-2-butyl]-2-chloroadenosine

Participants

Reaction Steps

The title compound was prepared according to general method A as described above in Example 1 by reacting 2-[(R)-2-amino-1-butylthio]benzothiazole hydrochloride (1.16 g, 4.2 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.57 g, 3.5 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-2-chloro-N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]adenosine using sodium methoxide in methanol. This provided the title N-[(R)-1-(2-benzothiazolyl)thio-2-butyl]-2-chloroadenosine (0.93 g, 51%) (following column chromatography), 1H NMR (DMSO-d6) δ 1.38 (3H, d, --CH2CH3), 1.65-1.86 (2H, m, --CH2CH3), 3.95 (1H, q, H-4'), 4.14 (1H, d, H-3'), 4.48-4.62 (2H, m, H-2' and --CHCH2H3), 5.07 (1H, t, 5'-OH), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.83 (1H, d, H-1'), 7.34, 7.45 (2H, 2t, Ar-H), 7.84, 8.0 (2H, 2d, Ar-H). HPLC retention time 21.8 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Provenance & Evidence