Stereoselective C-glycosylation of 2,3-dideoxyribofuranosides controlled by the methylenephosphonothioate functional groups at the 3-position

Heterocycles

Volumn 52, Issue 2, 2000, Pages 515-518

  Yokomatsu, Tsutomu ^a   Sada, Tomoyuki ^a   Shimizu, Takanori ^a   Shibuya, Shiroshi ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIDEOXYRIBOFURANOSIDE; DEOXYRIBONUCLEOTIDE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034143298     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-s56     Document Type: Article

References (20)

1. (a) D. W. Norbeck, Ann. Rep. Med. Chem., 1990, 25, 149.
2. (b) "Nucleoside & Nucleotides as Antitumor and Antiviral Agents," ed. by C. K. Chu and D. C. Baker, Plenum Press, New York, 1993.
3. H. Vorbrüggen, Acc. Chem. Res., 1995, 28, 509.
4. H. Vorbrüggen, K. Krolikiewict, and B. Bennya, Chem. Ber., 1981, 114, 1234.
5. Recent intramolecular N-glycosylation of 2-deoxyribofuranosides: (a) M. E. Jung and C. Castro, J. Org. Chem., 1993, 58, 807.
6. (b) K. Sujino and H. Sugimura, Chem. Lett., 1993, 1187.
7. (c) K. Sujino and H. Sugimura, Tetrahedron Lett., 1994, 35, 1883 and references cited therein.
8. For an intramolecular approach to stereoselective synthesis of a metabolically stable analogue of thymidine 3′-phosphate: T. Yokomatsu, T. Shimizu, T. Sada, and S. Shibuya, Heterocycles, 1999, 50, 21.
9. (a) T. Oguchi, H. Kubota, and K. Narasaka, Chem. Lett., 1989, 801.
10. (b) J.-F. Lavallee and G. Just, Tetrahedron Lett., 1991, 32, 3469.
11. (c) T. Mukaiyama, N. Hirano, M. Nishida, and H. Uchiro, Chem. Lett., 1996, 99.
12. T. Yokomatsu, T. Sada, T. Shimizu, and S. Shibuya, Tetrahedron Lett., 1998, 39, 6299.
13. Reviews for C-nucleoside analogues: a) K. A. Watanabe, "The Chemistry of C-Nucleosides," in "Chemistry of Nucleoside and Nucleotides," ed. by L.B. Townsend, Plenum Press, New York, 1994, Vol 3, p. 421.
14. b) L. J. S. Knutsen, Nucleosides & Nucleotides, 1992, 11, 961.
15. (c) M. H. D. Postema, Tetrahedron, 1992, 48, 8545.
16. (d) N. C. Chaudhuri, R. X.-F. Ren, and E. T. Kool, Synthesis, 1997, 341.
17. An epimerization of the anomeric center of the substrate was observed when the β-anomer of 1 was used as a glycosyl donor.
18. 5PS: C, 58.23; H, 7.09. Found: C, 58.68; H, 7.30.
19. For nucleophile-dependent allylation reactions: (a) Y. Yamamoto, S. Nishi, and J. Yamada, J. Am. Chem. Soc., 1986, 108, 7116.
20. (b) T. Sato, J. Otera, and H. Nozaki, J. Org. Chem., 1990, 55, 6116.