Novel lewis acid-catalyzed rearrangement of a sugar-base hybrid to afford an anhydronucleoside

Nucleosides and Nucleotides

Volumn 17, Issue 12, 1998, Pages 2383-2387

  Jung, Michael E ^a   Castro, Claire ^a,b   Khan, Saeed I ^a  

^a UNIVERSITY OF SAN FRANCISCO   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6,3' ANHYDRO 2' DEOXYURIDINE; BORON DERIVATIVE; DEOXYURIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; GLYCOSYLATION; METHYLATION; MOLECULAR DYNAMICS; NUCLEOTIDE METABOLISM; REDUCTION; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0031757644     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319808004325     Document Type: Article

References (15)

1. Jung, M. E.; Castro, C. J. Org. Chem. 1993, 58, 807.
2. For other examples of intramolecular Vorbrüggen couplings, see: a) Sujino, K.; Sugimura, H. J. Chem. Soc., Chem. Commun. 1994, 2541; Tetrahedron Lett. 1994, 35, 1883; Chem. Lett. 1993, 1187. b) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides 1995, 14, 413. c) Mizuno, Y.; Kaneko, C.; Oikawa, Y.; Ikeda, T.; Itoh, T. J. Am. Chem. Soc. 1972, 94, 4737. d) Mizuno, Y.; Kaneko, C.; Oikawa, Y. J. Org. Chem. 1974, 39, 1440. e) El Subbagh, H. I.; Ping, L.-J.; Abushanab, E. Nucleosides Nucleotides 1992, 11, 603. f) Chemla, P. Tetrahedron Lett. 1993, 34, 7391.
3. For other examples of intramolecular Vorbrüggen couplings, see: a) Sujino, K.; Sugimura, H. J. Chem. Soc., Chem. Commun. 1994, 2541; Tetrahedron Lett. 1994, 35, 1883; Chem. Lett. 1993, 1187. b) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides 1995, 14, 413. c) Mizuno, Y.; Kaneko, C.; Oikawa, Y.; Ikeda, T.; Itoh, T. J. Am. Chem. Soc. 1972, 94, 4737. d) Mizuno, Y.; Kaneko, C.; Oikawa, Y. J. Org. Chem. 1974, 39, 1440. e) El Subbagh, H. I.; Ping, L.-J.; Abushanab, E. Nucleosides Nucleotides 1992, 11, 603. f) Chemla, P. Tetrahedron Lett. 1993, 34, 7391.
4. For other examples of intramolecular Vorbrüggen couplings, see: a) Sujino, K.; Sugimura, H. J. Chem. Soc., Chem. Commun. 1994, 2541; Tetrahedron Lett. 1994, 35, 1883; Chem. Lett. 1993, 1187. b) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides 1995, 14, 413. c) Mizuno, Y.; Kaneko, C.; Oikawa, Y.; Ikeda, T.; Itoh, T. J. Am. Chem. Soc. 1972, 94, 4737. d) Mizuno, Y.; Kaneko, C.; Oikawa, Y. J. Org. Chem. 1974, 39, 1440. e) El Subbagh, H. I.; Ping, L.-J.; Abushanab, E. Nucleosides Nucleotides 1992, 11, 603. f) Chemla, P. Tetrahedron Lett. 1993, 34, 7391.
5. For other examples of intramolecular Vorbrüggen couplings, see: a) Sujino, K.; Sugimura, H. J. Chem. Soc., Chem. Commun. 1994, 2541; Tetrahedron Lett. 1994, 35, 1883; Chem. Lett. 1993, 1187. b) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides 1995, 14, 413. c) Mizuno, Y.; Kaneko, C.; Oikawa, Y.; Ikeda, T.; Itoh, T. J. Am. Chem. Soc. 1972, 94, 4737. d) Mizuno, Y.; Kaneko, C.; Oikawa, Y. J. Org. Chem. 1974, 39, 1440. e) El Subbagh, H. I.; Ping, L.-J.; Abushanab, E. Nucleosides Nucleotides 1992, 11, 603. f) Chemla, P. Tetrahedron Lett. 1993, 34, 7391.
6. For other examples of intramolecular Vorbrüggen couplings, see: a) Sujino, K.; Sugimura, H. J. Chem. Soc., Chem. Commun. 1994, 2541; Tetrahedron Lett. 1994, 35, 1883; Chem. Lett. 1993, 1187. b) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides 1995, 14, 413. c) Mizuno, Y.; Kaneko, C.; Oikawa, Y.; Ikeda, T.; Itoh, T. J. Am. Chem. Soc. 1972, 94, 4737. d) Mizuno, Y.; Kaneko, C.; Oikawa, Y. J. Org. Chem. 1974, 39, 1440. e) El Subbagh, H. I.; Ping, L.-J.; Abushanab, E. Nucleosides Nucleotides 1992, 11, 603. f) Chemla, P. Tetrahedron Lett. 1993, 34, 7391.
7. For other examples of intramolecular Vorbrüggen couplings, see: a) Sujino, K.; Sugimura, H. J. Chem. Soc., Chem. Commun. 1994, 2541; Tetrahedron Lett. 1994, 35, 1883; Chem. Lett. 1993, 1187. b) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides 1995, 14, 413. c) Mizuno, Y.; Kaneko, C.; Oikawa, Y.; Ikeda, T.; Itoh, T. J. Am. Chem. Soc. 1972, 94, 4737. d) Mizuno, Y.; Kaneko, C.; Oikawa, Y. J. Org. Chem. 1974, 39, 1440. e) El Subbagh, H. I.; Ping, L.-J.; Abushanab, E. Nucleosides Nucleotides 1992, 11, 603. f) Chemla, P. Tetrahedron Lett. 1993, 34, 7391.
8. For other examples of intramolecular Vorbrüggen couplings, see: a) Sujino, K.; Sugimura, H. J. Chem. Soc., Chem. Commun. 1994, 2541; Tetrahedron Lett. 1994, 35, 1883; Chem. Lett. 1993, 1187. b) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides 1995, 14, 413. c) Mizuno, Y.; Kaneko, C.; Oikawa, Y.; Ikeda, T.; Itoh, T. J. Am. Chem. Soc. 1972, 94, 4737. d) Mizuno, Y.; Kaneko, C.; Oikawa, Y. J. Org. Chem. 1974, 39, 1440. e) El Subbagh, H. I.; Ping, L.-J.; Abushanab, E. Nucleosides Nucleotides 1992, 11, 603. f) Chemla, P. Tetrahedron Lett. 1993, 34, 7391.
9. For other examples of intramolecular Vorbrüggen couplings, see: a) Sujino, K.; Sugimura, H. J. Chem. Soc., Chem. Commun. 1994, 2541; Tetrahedron Lett. 1994, 35, 1883; Chem. Lett. 1993, 1187. b) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides 1995, 14, 413. c) Mizuno, Y.; Kaneko, C.; Oikawa, Y.; Ikeda, T.; Itoh, T. J. Am. Chem. Soc. 1972, 94, 4737. d) Mizuno, Y.; Kaneko, C.; Oikawa, Y. J. Org. Chem. 1974, 39, 1440. e) El Subbagh, H. I.; Ping, L.-J.; Abushanab, E. Nucleosides Nucleotides 1992, 11, 603. f) Chemla, P. Tetrahedron Lett. 1993, 34, 7391.
10. Several methods exist for the hydrogenolysis of phenols to give the corresponding arenes. For an example, see: Musliner, W. J.; Gates, J. W., Jr. J. Am. Chem. Soc. 1966, 88, 4271.
11. Ichikawa, Y.; Kubota, H.; Fujita, K.; Okauchi, T.; Narasaka, K. Bull. Chem. Soc. Jpn. 1989, 62, 845.
12. The procedure for forming 7αβ involved addition of powdered KOH to a solution of the methyl ribosides 6αβ and Mel in DMSO and stirring at ambient temperature for 5h. Desilylation was effected by the normal technique (TBAF and the silyl ether were stirred together in THF for 1.5 h at ambient temperature). The proton NMR spectra of 7αβ corroborate their structures, e.g., the OH proton of 7β is a dd (J = 9, 3.3 Hz) coupled to the two C5 protons, and therefore no shift of the TBS group from the oxygen at C3 to that at C5 occurred during the base-promoted methylation. We thank the referee for suggesting that possibility.
13. Such intramolecular Vorbrüggen reactions from the 3′-position to the anomeric center proceed in reasonable yields, a) Xia, X.; Wang, J.; Hager, M. W.; Sisti, N.; Liotta, D. C. Tetrahedron Lett. 1997, 38, 1111. b) Jung, M. E.; Castro, C.; Yang, E. unpublished results.
14. Such intramolecular Vorbrüggen reactions from the 3′-position to the anomeric center proceed in reasonable yields, a) Xia, X.; Wang, J.; Hager, M. W.; Sisti, N.; Liotta, D. C. Tetrahedron Lett. 1997, 38, 1111. b) Jung, M. E.; Castro, C.; Yang, E. unpublished results.
15. Iver, V. K.; Horowitz, J. P. J. Org. Chem. 1982, 47, 644.