SCOPUS 정보 검색 플랫폼

Volumn 63, Issue 3, 1998, Pages 746-754

Stereo- And Regioselective Introduction of 1- or 2-Hydroxyethyl Group via Intramolecular Radical Cyclization Reaction with a Novel Silicon-Containing Tether. An Efficient Synthesis of 4′α-Branched 2′-Deoxyadenosines

(5) Shuto, Satoshi a Kanazaki, Makiko a Ichikawa, Satoshi a Minakawa, Noriaki a Matsuda, Akira a

a HOKKAIDO UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000927845 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo971703a Document Type: Article

Times cited : (67)

References (126)

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15
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- Studies on 2′-branched nucleosides, for examples: (a) Jenkins, S. R.; Arison, B.; Walton, E. J. Org. Chem. 1968, 33, 2490-2494. (b) Beigelman, L. N.; Ermolinsky, B. S.; Gurskaya, G. V.; Tsapkina, E. N.; Karpeisky, M. Y.; Mikhailov, S. N. Carbohydr. Res. 1987, 166, 219-232. (c) MaCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7400. (d) Lin, T. S.; Luo, M.-Z.; Liu, M.-C.; Clarke-Katzenberg, R. H.; Cheng, Y.-C.; Prusoff, W. H.; Mancini, W. R.; Birnbaum, G. I.; Gabe, E. J.; Giziewicz, J. J. Med. Chem. 1991, 34, 2607-2615. (e) Samano, V.; Robins, M. J. J. Am. Chem. Soc. 1992, 114, 4007-4008. (f) De Mesmaeker, A.; Lebreton, J.; Hoffmann, P.; Freier, S. M. Synlett 1993, 677-679. (g) Cicero, D. O.; Neuner, P. J. S.; Franzese, O.; D'Onofrio, C.; Iribarren, A. M. Bioorg. Med. Chem. Lett. 1994, 4, 861-866. (h) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S. Bioorg. Med. Chem. Lett. 1994, 4, 721-724. (i) Wimalasena, K.; Mahindaratne, M. P. D. J. Org. Chem. 1994, 59, 3427-3432. (j) Lawrence, A. J.; Pavey, J. B. J.; O'Neil, I. A.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341-6344. (k) Beigelman, L.; Karpeisky, A.; Matulic-Adamic, J.; Haeberli, P.; Sweedler, D.; Usman, N. Nucleic Acids Res. 1995, 23, 4434-4442.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 4007-4008
- Samano, V.¹ Robins, M.J.²

16
- 0002582138
- Studies on 2′-branched nucleosides, for examples: (a) Jenkins, S. R.; Arison, B.; Walton, E. J. Org. Chem. 1968, 33, 2490-2494. (b) Beigelman, L. N.; Ermolinsky, B. S.; Gurskaya, G. V.; Tsapkina, E. N.; Karpeisky, M. Y.; Mikhailov, S. N. Carbohydr. Res. 1987, 166, 219-232. (c) MaCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7400. (d) Lin, T. S.; Luo, M.-Z.; Liu, M.-C.; Clarke-Katzenberg, R. H.; Cheng, Y.-C.; Prusoff, W. H.; Mancini, W. R.; Birnbaum, G. I.; Gabe, E. J.; Giziewicz, J. J. Med. Chem. 1991, 34, 2607-2615. (e) Samano, V.; Robins, M. J. J. Am. Chem. Soc. 1992, 114, 4007-4008. (f) De Mesmaeker, A.; Lebreton, J.; Hoffmann, P.; Freier, S. M. Synlett 1993, 677-679. (g) Cicero, D. O.; Neuner, P. J. S.; Franzese, O.; D'Onofrio, C.; Iribarren, A. M. Bioorg. Med. Chem. Lett. 1994, 4, 861-866. (h) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S. Bioorg. Med. Chem. Lett. 1994, 4, 721-724. (i) Wimalasena, K.; Mahindaratne, M. P. D. J. Org. Chem. 1994, 59, 3427-3432. (j) Lawrence, A. J.; Pavey, J. B. J.; O'Neil, I. A.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341-6344. (k) Beigelman, L.; Karpeisky, A.; Matulic-Adamic, J.; Haeberli, P.; Sweedler, D.; Usman, N. Nucleic Acids Res. 1995, 23, 4434-4442.
- (1993) Synlett , pp. 677-679
- De Mesmaeker, A.¹ Lebreton, J.² Hoffmann, P.³ Freier, S.M.⁴

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- 0028260068
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- Cicero, D.O.¹ Neuner, P.J.S.² Franzese, O.³ D'Onofrio, C.⁴ Iribarren, A.M.⁵

18
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- Studies on 2′-branched nucleosides, for examples: (a) Jenkins, S. R.; Arison, B.; Walton, E. J. Org. Chem. 1968, 33, 2490-2494. (b) Beigelman, L. N.; Ermolinsky, B. S.; Gurskaya, G. V.; Tsapkina, E. N.; Karpeisky, M. Y.; Mikhailov, S. N. Carbohydr. Res. 1987, 166, 219-232. (c) MaCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7400. (d) Lin, T. S.; Luo, M.-Z.; Liu, M.-C.; Clarke-Katzenberg, R. H.; Cheng, Y.-C.; Prusoff, W. H.; Mancini, W. R.; Birnbaum, G. I.; Gabe, E. J.; Giziewicz, J. J. Med. Chem. 1991, 34, 2607-2615. (e) Samano, V.; Robins, M. J. J. Am. Chem. Soc. 1992, 114, 4007-4008. (f) De Mesmaeker, A.; Lebreton, J.; Hoffmann, P.; Freier, S. M. Synlett 1993, 677-679. (g) Cicero, D. O.; Neuner, P. J. S.; Franzese, O.; D'Onofrio, C.; Iribarren, A. M. Bioorg. Med. Chem. Lett. 1994, 4, 861-866. (h) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S. Bioorg. Med. Chem. Lett. 1994, 4, 721-724. (i) Wimalasena, K.; Mahindaratne, M. P. D. J. Org. Chem. 1994, 59, 3427-3432. (j) Lawrence, A. J.; Pavey, J. B. J.; O'Neil, I. A.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341-6344. (k) Beigelman, L.; Karpeisky, A.; Matulic-Adamic, J.; Haeberli, P.; Sweedler, D.; Usman, N. Nucleic Acids Res. 1995, 23, 4434-4442.
- (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 721-724
- Yoshimura, Y.¹ Saitoh, K.² Ashida, N.³ Sakata, S.⁴

19
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- Studies on 2′-branched nucleosides, for examples: (a) Jenkins, S. R.; Arison, B.; Walton, E. J. Org. Chem. 1968, 33, 2490-2494. (b) Beigelman, L. N.; Ermolinsky, B. S.; Gurskaya, G. V.; Tsapkina, E. N.; Karpeisky, M. Y.; Mikhailov, S. N. Carbohydr. Res. 1987, 166, 219-232. (c) MaCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7400. (d) Lin, T. S.; Luo, M.-Z.; Liu, M.-C.; Clarke-Katzenberg, R. H.; Cheng, Y.-C.; Prusoff, W. H.; Mancini, W. R.; Birnbaum, G. I.; Gabe, E. J.; Giziewicz, J. J. Med. Chem. 1991, 34, 2607-2615. (e) Samano, V.; Robins, M. J. J. Am. Chem. Soc. 1992, 114, 4007-4008. (f) De Mesmaeker, A.; Lebreton, J.; Hoffmann, P.; Freier, S. M. Synlett 1993, 677-679. (g) Cicero, D. O.; Neuner, P. J. S.; Franzese, O.; D'Onofrio, C.; Iribarren, A. M. Bioorg. Med. Chem. Lett. 1994, 4, 861-866. (h) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S. Bioorg. Med. Chem. Lett. 1994, 4, 721-724. (i) Wimalasena, K.; Mahindaratne, M. P. D. J. Org. Chem. 1994, 59, 3427-3432. (j) Lawrence, A. J.; Pavey, J. B. J.; O'Neil, I. A.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341-6344. (k) Beigelman, L.; Karpeisky, A.; Matulic-Adamic, J.; Haeberli, P.; Sweedler, D.; Usman, N. Nucleic Acids Res. 1995, 23, 4434-4442.
- (1994) J. Org. Chem. , vol.59 , pp. 3427-3432
- Wimalasena, K.¹ Mahindaratne, M.P.D.²

20
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- Studies on 2′-branched nucleosides, for examples: (a) Jenkins, S. R.; Arison, B.; Walton, E. J. Org. Chem. 1968, 33, 2490-2494. (b) Beigelman, L. N.; Ermolinsky, B. S.; Gurskaya, G. V.; Tsapkina, E. N.; Karpeisky, M. Y.; Mikhailov, S. N. Carbohydr. Res. 1987, 166, 219-232. (c) MaCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7400. (d) Lin, T. S.; Luo, M.-Z.; Liu, M.-C.; Clarke-Katzenberg, R. H.; Cheng, Y.-C.; Prusoff, W. H.; Mancini, W. R.; Birnbaum, G. I.; Gabe, E. J.; Giziewicz, J. J. Med. Chem. 1991, 34, 2607-2615. (e) Samano, V.; Robins, M. J. J. Am. Chem. Soc. 1992, 114, 4007-4008. (f) De Mesmaeker, A.; Lebreton, J.; Hoffmann, P.; Freier, S. M. Synlett 1993, 677-679. (g) Cicero, D. O.; Neuner, P. J. S.; Franzese, O.; D'Onofrio, C.; Iribarren, A. M. Bioorg. Med. Chem. Lett. 1994, 4, 861-866. (h) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S. Bioorg. Med. Chem. Lett. 1994, 4, 721-724. (i) Wimalasena, K.; Mahindaratne, M. P. D. J. Org. Chem. 1994, 59, 3427-3432. (j) Lawrence, A. J.; Pavey, J. B. J.; O'Neil, I. A.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341-6344. (k) Beigelman, L.; Karpeisky, A.; Matulic-Adamic, J.; Haeberli, P.; Sweedler, D.; Usman, N. Nucleic Acids Res. 1995, 23, 4434-4442.
- (1995) Tetrahedron Lett. , vol.36 , pp. 6341-6344
- Lawrence, A.J.¹ Pavey, J.B.J.² O'Neil, I.A.³ Cosstick, R.⁴

21
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- Studies on 2′-branched nucleosides, for examples: (a) Jenkins, S. R.; Arison, B.; Walton, E. J. Org. Chem. 1968, 33, 2490-2494. (b) Beigelman, L. N.; Ermolinsky, B. S.; Gurskaya, G. V.; Tsapkina, E. N.; Karpeisky, M. Y.; Mikhailov, S. N. Carbohydr. Res. 1987, 166, 219-232. (c) MaCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7400. (d) Lin, T. S.; Luo, M.-Z.; Liu, M.-C.; Clarke-Katzenberg, R. H.; Cheng, Y.-C.; Prusoff, W. H.; Mancini, W. R.; Birnbaum, G. I.; Gabe, E. J.; Giziewicz, J. J. Med. Chem. 1991, 34, 2607-2615. (e) Samano, V.; Robins, M. J. J. Am. Chem. Soc. 1992, 114, 4007-4008. (f) De Mesmaeker, A.; Lebreton, J.; Hoffmann, P.; Freier, S. M. Synlett 1993, 677-679. (g) Cicero, D. O.; Neuner, P. J. S.; Franzese, O.; D'Onofrio, C.; Iribarren, A. M. Bioorg. Med. Chem. Lett. 1994, 4, 861-866. (h) Yoshimura, Y.; Saitoh, K.; Ashida, N.; Sakata, S. Bioorg. Med. Chem. Lett. 1994, 4, 721-724. (i) Wimalasena, K.; Mahindaratne, M. P. D. J. Org. Chem. 1994, 59, 3427-3432. (j) Lawrence, A. J.; Pavey, J. B. J.; O'Neil, I. A.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341-6344. (k) Beigelman, L.; Karpeisky, A.; Matulic-Adamic, J.; Haeberli, P.; Sweedler, D.; Usman, N. Nucleic Acids Res. 1995, 23, 4434-4442.
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- Beigelman, L.¹ Karpeisky, A.² Matulic-Adamic, J.³ Haeberli, P.⁴ Sweedler, D.⁵ Usman, N.⁶

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- (1968) J. Org. Chem. , vol.33 , pp. 1789-1795
- Nutt, R.F.¹ Dickinson, M.J.² Holly, F.W.³ Walton, E.⁴

23
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- Hayakawa, H.¹ Tanaka, H.² Itoh, N.³ Nakajima, M.⁴ Miyasaka, T.⁵ Yamaguchi, K.⁶ Iitaka, Y.⁷

24
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- (1991) Tetrahedron , vol.47 , pp. 1727-1736
- Huss, S.¹ De Las Heras, F.G.² Camarasa, M.J.³

25
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- Studies on 3′-branched nucleosides, for examples: (a) Nutt, R. F.; Dickinson, M. J.; Holly, F. W.; Walton, E. J. Org. Chem. 1968, 33, 1789-1795. (b) Hayakawa, H.; Tanaka, H.; Itoh, N.; Nakajima, M.; Miyasaka, T.; Yamaguchi, K.; Iitaka, Y. Chem. Pharm. Bull. 1987, 35, 2605-2608. (c) Huss, S.; De las Heras, F. G.; Camarasa, M. J. Tetrahedron 1991, 47, 1727-1736. (d) Bender, S. L.; Moffett, K. K. J. Org. Chem. 1992, 57, 1646-1647. (e) Lee, K.; Wiemer, D. F. J. Org. Chem. 1993, 58, 7808-7812, (f) Jorgensen, P. N.; Stein, P. C.; Wengel, J. J. Am. Chem. Soc. 1994, 116, 2231-2232. (g) Schmit, C.; Bevierre, M.-O.; De Mesmaeker, A.; Altamann, K.-H. Bioorg. Med. Chem. Lett. 1994, 4, 1969-1974. (h) Hossain, N.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4167-4178. (i) Johnson, C. R.; Rhumralkar, D. R.; De Clercq, E. Nucleosides Nucleotides 1995, 14, 185-194. (j) Becouarn, S.; Szernecki, S.; Valery, J.-M. Tetrahedron Lett. 1995, 36, 873-876. (k) Jung, P. M. J.; Burger, A.; Biellmann, J.-F. Tetrahedron Lett. 1995, 36, 1031-1034. (l) Auguste, S. P.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1995, 395-404.
- (1992) J. Org. Chem. , vol.57 , pp. 1646-1647
- Bender, S.L.¹ Moffett, K.K.²

26
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- (1993) J. Org. Chem. , vol.58 , pp. 7808-7812
- Lee, K.¹ Wiemer, D.F.²

27
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- (1994) J. Am. Chem. Soc. , vol.116 , pp. 2231-2232
- Jorgensen, P.N.¹ Stein, P.C.² Wengel, J.³

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