Highly stereoselective synthesis of 2'-deoxy-α-ribonucleosides and 2-deoxy-α-C-ribofuranosides by remote stereocontrolled glycosylation

Chemistry Letters

Volumn , Issue 4, 1997, Pages 389-390

  Mukaiyama, Teruaki ^a   Ishikawa, Tatsuya ^a   Uchiro, Hiromi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001740414     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.389     Document Type: Article

References (14)

1. L. J. Wilson, M. W. Hager, Y. A. El-Kattan, and D. C. Liotta, Synthesis, 1995, 1465; D. M. Huryn and M. Okabe, Chem. Rev., 92, 1745(1992); K. A. Watanabe, "The Chemistry of C-Nucleosides," in "Chemistry of Nucleosides and Nucleotides," ed by L. B. Townsend, Plenum, New York (1994), vol. 3, p. 421, and References cited therein.
2. L. J. Wilson, M. W. Hager, Y. A. El-Kattan, and D. C. Liotta, Synthesis, 1995, 1465; D. M. Huryn and M. Okabe, Chem. Rev., 92, 1745(1992); K. A. Watanabe, "The Chemistry of C-Nucleosides," in "Chemistry of Nucleosides and Nucleotides," ed by L. B. Townsend, Plenum, New York (1994), vol. 3, p. 421, and References cited therein.
3. L. J. Wilson, M. W. Hager, Y. A. El-Kattan, and D. C. Liotta, Synthesis, 1995, 1465; D. M. Huryn and M. Okabe, Chem. Rev., 92, 1745(1992); K. A. Watanabe, "The Chemistry of C-Nucleosides," in "Chemistry of Nucleosides and Nucleotides," ed by L. B. Townsend, Plenum, New York (1994), vol. 3, p. 421, and References cited therein.
4. T. Mukaiyama, N. Hirano, M. Nishida, and H. Uchiro, Chem. Lett., 1996, 99.
5. T. Mukaiyama, H. Uchiro, N. Hirano, and T. Ishikawa, Chem. Lett., 1996, 629.
6. G. A. LaPage and I. G. Junga, Mol. Pharmacol., 2, 37(1967).
7. T. Yamaguchi and M. Saneyoshi, Chem. Pharm. Bull., 32, 1441(1984).
8. E. Uhlmann and A. Peyman, Chem. Rev., 90, 543(1990), and References cited therein.
9. Syntheses of 2'-deoxy-α-ribonucleosides: H. Aoyama, Bull. Chem. Soc. Jpn., 60, 2073(1987); H. Sugimura, K. Sujino, and K. Osumi, Nucleic Acids Symp. Ser., 27, 111(1992). Syntheses of 2-deoxy-α-C-ribofuranosides: J. Uenishi, A. Sohma, and O. Yonemitsu, Chem. Lett., 1996, 595.
10. Syntheses of 2'-deoxy-α-ribonucleosides: H. Aoyama, Bull. Chem. Soc. Jpn., 60, 2073(1987); H. Sugimura, K. Sujino, and K. Osumi, Nucleic Acids Symp. Ser., 27, 111(1992). Syntheses of 2-deoxy-α-C-ribofuranosides: J. Uenishi, A. Sohma, and O. Yonemitsu, Chem. Lett., 1996, 595.
11. Syntheses of 2'-deoxy-α-ribonucleosides: H. Aoyama, Bull. Chem. Soc. Jpn., 60, 2073(1987); H. Sugimura, K. Sujino, and K. Osumi, Nucleic Acids Symp. Ser., 27, 111(1992). Syntheses of 2-deoxy-α-C-ribofuranosides: J. Uenishi, A. Sohma, and O. Yonemitsu, Chem. Lett., 1996, 595.
12. The possibility of such α-selective glycosylation of 2-deoxyribose was shown by Wierenga et al. in 1981 by use of unstable 5-O-toluoyl halosugar, however, the yield of desired 2'-deoxy-α-ribonucleoside in this reaction was 4%: W. Wierenga and H. I. Skulnick, Carbohydr. Res., 90, 41(1981).
13. This glycosyl donor was prepared from methyl 2-deoxy-D-ribofuranoside shown in the following scheme. formula presented
14. Silyl triflates, SiCl2(OTf)2 and SiCl(OTf)3, were prepared from SiCl4 and two or three molar equivalents of AgOTf in toluene and stocked as this solution.