Sodium Methoxide → 5'-O-acetyl-2-chloro-N-{(R)-1-[5-phenyl-(1,2,4-triazol-3yl)]thio-2-propyl}adenosine

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Reaction Steps

Partial deacylation of the purified 2',3',5'-Tri-O-acetyl-2-chloro-N-{(R)-1-[5-phenyl-(1,2,4-triazol-3-yl)]thio-2-propyl}adenosine (described in Example 27) using sodium methoxide in methanol to provide the title 5'-O-acetyl-2-chloro-N-{(R)-1-[5-phenyl-(1,2,4-triazol-3yl) ]thio-2-propyl}-adenosine (0.035 g, 8%) as a foam after column chromatography. 1H NMR (DMSO-d6) δ 1.34 (3H, d, --CHCH3), 2.02 (3H, s, --COCH3), 4.53-4.68 (2H, q, H-2' and --CHCH3), 5.40, 5.61 (2H, 2d, 2'- and 3'-OH), 5.86 (1H, d, H-1'), 7.38-8.01 (5H, 3m, Ar-H), 8.37 (1H, s, H-2). HPLC retention time 16.9 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Provenance & Evidence