Synthesis of 1,5-Anhydro-2-(N⁶-Cyclopentyladenin-9-Yl)-2-Deoxy-D-Altrohexitol

References

• Williams , M. 1987 . Ann. Rev. Pharmacol. Toxicol. , 27 : 315 – 345 .
   PubMed Web of Science ®Google Scholar
• Van Calker , D. , Müller , M. and Hamprecht , B. 1979 . J. Neurochem. , 33 : 999 – 1005 .
   PubMed Web of Science ®Google Scholar
• Londos , C. , Coopers , D. and Wolff , J. 1980 . J. Proc. Natl. Acad. Sci. U.S.A. , 77 : 2551 – 2554 .
   PubMed Web of Science ®Google Scholar
• Moos , W. , Szotek , S. and Bruns , R. 1985 . J. Med. Chem. , 28 : 1383 – 1384 .
   PubMed Web of Science ®Google Scholar
• Van Galen , P. , Leussen , F. , Ijzerman , A. and Soudijn , W. 1989 . Eur. J. Pharmacol. - Mol. Pharmacol. Sect. , 172 : 19 – 27 .
   PubMed Web of Science ®Google Scholar
• Verheggen , I. , Van Aerschot , A. , Toppet , S. , Snoeck , R. , Janssen , G. , Balzarini , J. , De Clercq , E. and Herdewijn , P. 1993 . J. Med. Chem. , 36 : 2033 – 2040 .
   PubMed Web of Science ®Google Scholar
• Analysis of compound 3: Mp: 219–222°C; UV(MeOH): λmax 262 nm (ε = 12000); CIMS (iC4H10): m/e 282 (MH+), 136 (BH2 +). 1H NMR (DMSO-d6): δ 3.42–3.78 (m, 4H), 4.09 (m, 3H), 4.57 (m, 1H), 4.68 (t, 1H, 6′-OH), 4.76 (d, 1H), 5.46 (d, 1H, J = 4 Hz), 7.26 (s, 2H, NH2), 8.17 (s, 1H), 8.35 (s, 1H) (H-2, H-8) ppm. 13C NMR (DMSO-d6): δ 55.4 (C-2′), 60.5 (C-6′), 63.6, 64.3 (C-3′, C-4′), 67.7 (C-1′), 77.4 (C-5′), 118.4 (C-5), 140.3 (C-8), 149.9 (C-4), 152.8 (C-2), 156.1 (C-6) ppm. Anal. (C11H15N5O4xH2O)C, H, N.
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• Analysis of compound 4: UV(MeOH): λmax 271 nm (ε = 12000); FDMS: m/e 350 (MH+), 204 (BH2 +); exact mass calculated for C16H23N5O4: 349.1750, found: 349.1812; 1H NMR (CDCl3): δ 1.05–2.35 (m, 9H, cyclopentyl), 3.42–3.80 (m, 4H), 4.10 (m, 3H), 4.57 (d, 1H), 4.76 (t, 1H, 6′-OH), 4.79 (d, 1H), 5.47 (d, J = 4 Hz, 1H), 7.32 (d, J = 8 Hz, 1H, NH), 8.22 (s, 1H), 8.28 (s, 1H) (H-2, H-8) ppm; 13C NMR (CDCl3): δ 23.6 (CH2), 33.3 (CH2), 52.3 (CH), 55.6 (C-2′), 60.8 (C-6′), 63.8, 64.4 (C-3′, C-4′), 68.0 (C-1′), 77.4 (C-5′), 119.1 (C-5), 138.4 (C-8), 149.2 (C-4), 153.5 (C-2), 154.5 (C-6) ppm. Anal. (C16H23N5O4x0.75H2O)
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• Taylor , M. D. , Moos , W. H. , Hamilton , H. W. , Szotek , D. S. , Patt , W. C. , Badger , E. W. , Bristol , J. A. , Bruns , R. F. , Heffner , T. G. and Mertz , T. E. 1986 . J. Med. Chem. , 29 : 346 – 353 .
   PubMed Web of Science ®Google Scholar