Sodium Methoxide → 2-chloro-N-[(S)-1-(2-benzothiazolyl)thio-2propyl]adenosine

Participants

Reaction Steps

The title compound was prepared according to general method A as described above in Example 1 by reacting 2-[(S)-2-amino-1-propylthio]benzothiazole hydrochloride [prepared by a Mitsunobu reaction as laid out in Example 1 using 2-[(S)-N-tert-butyloxycarbonyl]amino-1-propanol (3.5 g, 20 mmol) and 2-mercaptobenzothiazole (3.35 g, 20 mmol) followed by acidic hydrolysis] (1.1 g, 4.2 mmol) with 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.8 g, 4.5 mmol), followed by debenzoylation of the purified 2',3',5'-tri-O-benzoyl-2-chloro-N-[(S)-1-(2-benzothiazolyl)thio-2-propyl]adenosine using sodium methoxide in methanol to provide the title 2-chloro-N-[(S)-1-(2-benzothiazolyl)thio-2propyl]adenosine (0.88 g, 49%) (following column chromatography), 1H NMR (DMSO-d6) δ 1.38 (3H, d, --CHCH3), 3.50-3.68 (4H, m, H-5'a, and H-5'b and --CH2 --), 3.95 (1H, d, H-4'), 4.12 (1H, d, H-3'), 4.51 (1H, q, H-2'), 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), 7.85, 7.98 (2H, 2d, Ar-H), 8.40 (1H, s, H-8), 8.52 (1H, s, N--H). HPLC retention time 20.1 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Provenance & Evidence