6
L.-L. CHEN, X. MING, AND J.-D. CEN
(b) Li, J. Z.; Gao, L. X.; Ding, M. X. The chemical resolution of racemic cis-2-
hydroxymethyl-5-(cytosine-10-yl)-1,3-oxathiolane (BCH-189)-one direct method to obtain
lamivudine as anti-HIV and anti-HBV agent. Synth. Commun. 2002, 32, 2355–2359; (c)
Brown, N. A. Lamivudine for chronic hepatitis B: Efficacy, safety, resistance, and current
treatment issues. Front. Viral. Hepat. 2003, 365–381.
3. FTC: (a) Hoong, L. K.; Strange, L. E.; Liotta, D. C.; Koszalka, G. W.; Burns, C. L.;
Schinazi, R. F. Enzyme-mediated enantioselective preparation of pure enantiomers of
the antiviral agent 20,30-dideoxy-5-fluoro-30-thiacytidine (FTC) and related compounds.
J. Org. Chem. 1992, 57, 5563–5565; (b) Jeong, L. S.; Schinazi, R. F.; Beach, J. W.;
Kim, H. O.; Nampail, S.; Shanmuganathan, K.; Alves, A. J.; McMillan, A.; Chu, C.
K.; Mathis, R. Asymmetric synthesis and biological evaluation of b-L-(2R,5S)- and a-
L-(2R,5R)-1,3-oxathiolane-pyrimidine and -purine nucleosides as potential anti-HIV
agents. J. Med. Chem. 1993, 36, 181–195; (c) Bang, L. M.; Scott, L. J. Emtricitabine:
An antiretroviral agent for HIV infection. Drugs 2003, 63, 2413–2424; (d) Cahn, P.
Emtricitabine: A new nucleoside analogue for once-daily antiretroviral therapy. Expert.
Opin. Investig. Drugs 2004, 13, 55–68.
4. L-ddC, L-FddC: (a) Lin, T. S.; Luo, M. Z.; Liu, M. C.; Pai, S. B.; Dutschman, G.. E.; Cheng,
Y. C. Synthesis and biological evaluation of 2’,30-dideoxy-L-pyrimidine nucleosides as
potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus
(HBV). J. Med. Chem. 1994, 37, 798–803; (b) Lin, T. S.; Luo, M. Z.; Liu, M. C.; Pai, S. B.;
Dutschman, G. E.; Cheng, Y. C. Antiviral activity of 20,30-dideoxy-b-L-5-fluoro-cytidine
(b-L-FddC) and 20,30-dideoxy-b-L-cytidine (b-L-ddC) aganist hepatitis B virus and human
immunodeficiency virus type 1 in vitro. Biochem. Pharmacol. 1994, 47, 171–174.
5. L-dT: (a) Fujimori, S.; Iwanami, N.; Hashimoto, Y.; Shudo, K. A convenient and
stereoselective synthesis of 2-deoxy-b-L-ribonucleosides. Nucleosides Nucleotides 1992,
11, 341–349; (b) Sorbera, L. A.; Castaner, J.; Castaner, R. M.; Bayes, M. Telbivudine:
Anti-HBV agent. Drugs. Fut. 2003, 28, 870–879; (c) Keam, S. J. Telbivudine. Drugs
2007, 67, 1917–1929; (d) Yuen, M.-F.; Lai, C.-L. Telbivudine for chronic hepatitis B:
The GLOBE trial. Future Virol. 2008, 3, 317–323.
6. L-FMAU: (a) Ma, T.; Pai, S. B.; Zhu, Y.-L.; Lin, J. S.; Shanmuganathan, K.; Du, J.; Wang,
C.; Kim, H.; Newton, M. G.; Cheng, Y.-C.; Chu, C. K. Structure–activity relationships of
1-(2-deoxy-2-fluoro-b-L-arabinofuranosyl)-pyrimidine nucleosides as anti-hepatitis B virus
agents. J. Med. Chem. 1996, 39, 2835–2843; (b) Du, J. F.; Choi, Y.; Lee, K.; Chun, B. K.;
Hong, J. H.; Chu, C. K. A practical synthesis of L-FMAU from L-arabinose. Nucleosides
Nucleotides 1999, 18, 187–195; (c) Sznaidman, M. L.; Almond, M. R.; Pesyan, A. New
synthesis of L-FMAU from L-arabinose. Nucleosides Nucleotides 2002, 21, 155–163.
7. (a) Fazio, F.; Schneider, M. P. A novel synthesis of 2-deoxy-L-ribose. Tetrahedron: Asym-
metry 2000, 11, 1869–1876; (b) Hashimoto, Y.; Iwanami, N.; Fujimori, S.; Shudo, K.
Enantio- and meso-DNAs: Preparation, characterization, and interaction with comp-
lementary nucleic acid. J. Am. Chem. Soc. 1993, 115, 9883.
8. L-arabinose: (a) Urata, H.; Ogura, E.; Shinohara, K.; Ureda, Y.; Akagi, M. Synthesis and
properties of mirror-image DNA. Nucl. Acids Res. 1992, 20, 3325–3332; (b) Jung, M. E.;
Xu, Y. Efficient syntheses of L-ribose and 2-deoxy-L-ribose from D-ribose and L-arabinose.
Tetrahedron Lett. 1997, 38, 4199–4202; (c) Zhang, W.-J.; Ramasamy, K. S.; Averett, D. R.
Improved synthesis of 2-deoxy-L-ribose. Nucleosides Nucleotides 1999, 18, 2357–2365; (d)
Chong, Y.; Chu, C. K. Efficient synthesis of 2-deoxy-L-erythro-pentose (2-deoxy-L-ribose)
from L-arabinose. Carbohydr. Res. 2002, 337, 397–402.
9. L-Ascorbic acid: Kim, K. S.; Ann, Y. H.; Hurh, E. Y.; Lee, E. J. Efficient synthesis of
2-deoxy-L-ribose starting from L-ascorbic acid. J. Korean Chem. Soc. 1994, 38, 783–784.
10. Barton, D. H. R.; McCombie, S. W. A new method for the deoxygenation of secondary
alcohols. J. Chem. Soc., Perkin Trans. 1 1975, 16, 1574–1585.