Facile preparation of α-acyloxyacetaldehyde, a versatile intermediate in the synthesis of antiviral nucleosides

Synthetic Communications

Volumn 34, Issue 11, 2004, Pages 1925-1930

  Du, Jinfa ^a   Watanabe, Kyoichi A ^a  

^a PHARMASSET INC   (United States)

Author keywords

HBV; HIV 1; Nucleosides; Synthesis

Indexed keywords

4 ACETOXY 2 ACYLOXYMETHYL 1,3 OXATHIOLANE; ACETAL DERIVATIVE; ACETALDEHYDE; ALPHA ACYLOXYACETALDEHYDE; ANTIVIRUS AGENT; LAMIVUDINE; NUCLEOSIDE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 2942661840     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120037904     Document Type: Article

References (28)

1. Belleau, B.; Dixit, D.; Nguyen-Ga, N.; Kraus, J.L. Design and activity of a novel class of nucleotide analogs effective against HIV-1, 5th International Conference on AIDS, Montreal, Canada, June 4-9, 1989, #T. C. O. 1.
2. Chu, C.K.; Ann, S.K.; Kim, H.O.; Beach, J.W.; Alves, A.J.; Jeong, L.S.; Islam, Q.; Van Roey, P.; Schinazi, R.F. Asymmetric synthesis of enantiomerically pure (-)-(1′R,4′R)-dioxolane-thymine and its anti-HIV activity. Tetrahedran Lett. 1991, 32 (31), 3791-3791.
3. Choi, W.B.; Wilson, L.J.; Yeola, S.; Liotta, D.C.; Schinazi, R.F. In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of thialanyl and dioxolanyl nucleoside analogs. J. Am. Chem. Soc. 1991, 113 (24), 9377-9379.
4. (a) Schinazi, R.F.; McMillan, A.; Cannon, D.; Mathis, R.; Lloyd, R.M.; Peck, A.; Sommadossi, J.P.; St. Clair, M.; Wilson, J.; Furman, P.A. Selective inhibition of human immunodeficiency viruses by racemates and enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine. Antimicrob. Agents Chemother. 1992, 36, 2423-2431;
5. (b) Liotta, D.C.; Schinazi, R.F.; Choi, W.-B. Method for the Synthesis, Compositions and Use of 2′-Deoxy-5-fluoro-3′-thiacytidine and Related Compounds. US Patent 5,210,085, May 11, 1993;
6. (c) Liotta, D.C.; Schinazi, R.F.; Choi, W.B. Antiviral Activity and Resolution of 2-Hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane. US Patent 5,914,331, Jun 22, 1999.
7. Kraus, J.L.; Attardo, G. Synthesis of new 2,5-substituted 1,3-oxathiolanes. Intermediates in nucleoside chemistry. Synthesis 1991, 1046-1048.
8. Belleau, B.; Nguyen-Ba, N. 2-Substituted-5-substituted-1,3-oxathiolanes with Antiviral Properties. US Patent 5,047,407, September 10, 1991.
9. Jin, H.; Siddiqui, M.A.; Evans, C.A.; Tse, H.L.A.; Mansour, T.S.A. Diastereoselective synthesis of the potent antiviral agent (-)-2′-deoxy- 3′-thiacytidine and its enantiomer. J. Org. Chem. 1995, 60 (8), 2621-2623.
10. 2 on active carbon. Org. Lett. 1999, 1 (5), 713-715.
11. Hann, R.M.; Maclay, W.D.; Hudson, C.S. The structures of the diacetone dulcitols. J. Am. Chem. Soc. 1939, 61 (9), 2432-2442.
12. Haskins, W.T.; Hann, R.M.; Hudson, C.S. The isomeric 1,3- and 2,3-benzylidene-D-arabitols. J. Am. Chem. Soc. 1943, 65 (9), 1663-1667.
13. (a) Sheikh, E. The vapor phase oxidation of alcohols by cupric oxide. A convenient preparation of aldehydes and ketones. Tetrahedron Lett. 1972, 13 (4), 257-260;
14. (b) Mancuso, A.J.; Swern, D. Activated dimethyl sulfoxide: useful reagents for synthesis. Synthesis 1981, 165-184;
15. (c) Bauer, M. Iodide catalysis of oxidations with dimethyl sulfoxide. Convenient two-step synthesis of α-diketones from α-methylene ketones. J. Org. Chem. 1975, 40 (13), 1990-1992;
16. (d) Hanessian, S. Oxidation of alcohols with N-halosuccinimidesnew and efficient variants. Synthesis 1981, 394-396.
17. Kornblum, N.; Jones, W.J.; Anderson, G.J. A new and selective method of oxidation. The conversion of alkyl halides and alkyl tosylates to aldehydes. J. Am. Chem. Soc. 1959, 81 (15), 4113-4114.
18. (a) Shiao, M.J.; Yang, C.Y.; Lee, S.H.; Wu, T.C. A convenient synthesis of protected α-hydroxyacetaldehyde. Synth. Commun. 1988, 18, 359;
19. (b) Hashiguchi, S.; Maeda, Y.; Kishimoto, S.; Ochiai, M. A study on the synthesis of carumonam starting from α-amino acid. Heterocycles 1986, 24, 2273.
20. Maehr, H.; Perrotta, A.; Smallheer, J. Synthetic (S)-5-(benzoyloxy)-6- oxohexanoic acid ethyl ester and S,S-(E)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester, important synthons for leukotrienes B4 and A4 from D-arabinose. J. Org. Chem. 1988, 53 (4), 832-836.
21. Chou, T.S.; Tsai, C.Y.; Lee, S.J. A cyclization approach toward five-membered heteroaromatic o-quinodimethanes via fused-3-sulfolenes. J. Chin. Chem. Soc. 1997, 44, 299-307.
22. Marshall, J.A.; Liao, J. Stereoselective total synthesis of the pseudopterolide kallolide A. J. Org. Chem. 1998, 63 (17), 5962-5970.
23. Painter, G.R.; Liotta, D.C.; Almond, M.R.; Cleary, D.G.; Soria, J.D.; Sznaidman, M. Method of Manufacture of 1,3-Oxathiolane Nucleosides. US Patent 6,215,004, April 10, 2001.
24. Hopkins, M.H.; Overman, L.E.; Rishton, G.M. Stereocontrolled preparation of tetrahydrofurans from acid-promoted rearrangements of allylic acetals. J. Am. Chem. Soc. 1991, 113 (14), 5354-5365.
25. Hambeck, R.; Just, G. A short synthesis of (±)-oxetanocin. Tetrahedron Lett. 1990, 31 (38), 5445-5448.
26. Rodrigruez, A.D.; Shi, J.G.; Shi, Y.P. Isolation, structural charactrization, and synthesis of naturally occurring bisfuranopseudopterane ether: biskallolide A. Evidence for a carbocation intermediate during the facile conversion of kallolide A and isokallolide A into various solvolysis products 2000, 65 (10), 3192-3199.
27. Grese, T.A.; Hutchinson, K.D.; Overman, L.E. General approach to halogenated tetrahydrofuran natural products from red algae of the genus Laurencia. Total synthesis of (±)-kumausallene and (±)-1-epi- kumausallene. J. Org. Chem. 1993, 58 (9), 2468-2477.
28. Hong, J.H.; Xu, Y.C.; Cha, M.; Shin, S.E.; Kim, J.H.; Chung, W.K.; Chun, M.W. Improved synthesis of D-1,3-oxathiolanyl acetate from D-mannose and D-galactose. Archiv. Pharmacol. Res. 1994, 17 (5), 383-385.