Ammonia → HCID 54487654, compound

Participants

Reaction Steps

2-(Phenylthiomethyl)piperidine was prepared from 2-(hydroxymethyl)piperidine by the method described by Kotsuki et al., Tetrahedron Letters, 1991, 32, 4155-4158; otherwise the synthesis proceeded as described in Example 16. 1-Amino-2-(phenylthiomethyl)piperidine (1.4 g, 6.5 mmol) was reacted with 9-(2',3',5'tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 3.25 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N-[2-(phenylthiomethyl)-1-piperidinyl]adenosine (0.17 g, 10%) as a foam (a mixture of diastereoisomers); 1H NMR (DMSO-d6) δ 3.51-3.59 (1H, m, H-5'a), 3.62-3.70 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.13 (1H, q, H-3'), 4.47-4.56 (1H, m, H-2'), 5.06 (1H, t, 5'-0H), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.82-5.87 (1H, 2d, H-1'), 7.16-7.54 (5H, 2m, Ar--H), 8.41, 8.46 (1H, 2s, H-8), 9.40 (1H, s, N--H).

Provenance & Evidence