Convenient synthesis of 4-C-branched lactones and 3'-C-branched 2',3'- dideoxynucleosides

Nucleosides and Nucleotides

Volumn 15, Issue 7-8, 1996, Pages 1361-1368

  Wengel, Jesper ^a   Østergaard, Kirsten ^a   Hager, Anders ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE;

ARTICLE; CATALYSIS; COLUMN CHROMATOGRAPHY; DRUG PURIFICATION; DRUG SELECTIVITY; STEREOCHEMISTRY;

EID: 0030015039     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319608002436     Document Type: Article

References (18)

1. The naturally occurring nucleoside oxetanocin A exhibits promising anti-HIV activity. Hoshino, H.; Shimizu, N.; Shimada, N.; Takita, T.; Takeuchi, T. J. Antibiot. 1987, 40, 1077.
2. 2',3'-Dideoxy-3'-C-hydroxymethyl nucleosides have shown anti-HIV activity. See e.g.: Svansson, L.; Kvarnström, I.; Classon, B.; Samuelsson, B. J. Org. Chem. 1991, 56, 2993 (cytosine derivative); Tseng, C. K.-H.; Marquez, V. E.; Milne, G. W. A.; Wysocki, Jr., R. J.; Mitsuya, H.; Shirasaki, T.; Driscoll, J. S. J. Med. Chem. 1991, 34, 343 (adenine derivative).
3. 2',3'-Dideoxy-3'-C-hydroxymethyl nucleosides have shown anti-HIV activity. See e.g.: Svansson, L.; Kvarnström, I.; Classon, B.; Samuelsson, B. J. Org. Chem. 1991, 56, 2993 (cytosine derivative); Tseng, C. K.-H.; Marquez, V. E.; Milne, G. W. A.; Wysocki, Jr., R. J.; Mitsuya, H.; Shirasaki, T.; Driscoll, J. S. J. Med. Chem. 1991, 34, 343 (adenine derivative).
4. For a report describing oligonudeotide analogues containing dephospho internucleoside linkages: De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366.
5. Mann, J.; Weymouth-Wilson, A. C. Carbohydr. Res. 1991, 216, 511.
6. Mann, J.; Weymouth-Wilson, A. C. Synlett 1992, 67.
7. Mann, J.; Weymouth-Wilson, A. C. J. Chem. Soc. Perkin Trans, 1 1994, 3141.
8. Brown, D.; Cardin, C. J.; Mann, J. J. Chem. Soc. Chem. Commun. 1995, 825.
9. Only a few β-D-threo-configurated 2',3'-dideoxynucleosides have been reported to exhibit anti-HIV activity: Tronchet, J. M. J.; Zsély, M.; Capek, K.; Komaromi, I.; Geoffroy, M.; De Clercq, E.; Balzarini, J. Nucleosides Nucleotides 1994, 13, 1871.
10. 6
11. This deoxygenation method has been reported earlier. Dolan, S. C.; MacMillan, J. J. Chem. Soc. Chem. Commun. 1985, 1588; Kakefuda, A.; Yoshimura, Y.; Sasaki, T.; Matsuda, A. Tetrahedron 1993, 49, 8513.
12. This deoxygenation method has been reported earlier. Dolan, S. C.; MacMillan, J. J. Chem. Soc. Chem. Commun. 1985, 1588; Kakefuda, A.; Yoshimura, Y.; Sasaki, T.; Matsuda, A. Tetrahedron 1993, 49, 8513.
13. Silylation was performed by a method described earlier. Nakamura, E.; Hashimoto, K.; Kuwajima, I. Bull. Chem. Soc. Jpn. 1981, 54, 805.
14. These reactions were performed by methods described earlier. Okabe, M.; Sun, R,-C.; Tarn, S. Y.-K.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1988, 53, 4780.
15. Wittenburg, E. Z. Chem. 1964, 1, 303.
16. Niedballa, U.; Vorbrüggen, H. J. Org. Chem. 1974, 39, 3654.
17. Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
18. When the main purpose is biological testing, evaluation of novel nucleosides as anomeric mixtures is a rational approach.