Nucleosides. 131. the Synthesis of 5-(2-Chloro-2-Deoxy-3-D-Arabino-Furanosyduracil. Reinterpretation of Reaction of ψ-Uridine with A-Acetoxyisobutyryl Chloride. Studies Directed Toward the Synthesis of 21-Deoxy-21-Substituted Arabinq-Nucleosides. 2

Krzysztof W. Pankiewicz; Kyoichi A. Watanabe

doi:10.1080/07328318508081894

Nucleosides. 131. the Synthesis of 5-(2-Chloro-2-Deoxy-3-D-Arabino-Furanosyduracil. Reinterpretation of Reaction of ψ-Uridine with A-Acetoxyisobutyryl Chloride. Studies Directed Toward the Synthesis of 2¹-Deoxy-2¹-Substituted Arabinq-Nucleosides. 2

Krzysztof W. Pankiewicz, Kyoichi A. Watanabe

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

Treatment of -uridine (3) with a-acetoxyisobutyryl chloride in acetonitrile gave, after deprotection, a mixture of four products: 5-(2-chloro-2-deoxy-B“D-arabinofuranosyljuracil (10a), its 3’-chloro xylo isomer (11a), 2^l-chloro-2'-deoxy--uridine (9a) and 4,2’-anhydro--uridine (8a). Each component was isolated by column chromatography. Compound 9 was converted to the known 1,3-dimethyl derivative 2 by treatment with DMF-dimethylacetal. Treatment of 10 and 1_1 with NaOMe/MeOH afforded the same 4,2’-anhydro-C-nucleoside 8. The 1,3-dimethyl analogues of TO and 11, however, were converted to 2‘,3’-anhydro-l,3-dimethyl-i(j-uridine (13) upon base treatment. The epoxide 13 was also prepared in good yield by treatment of 10 and 11_ with DMF-dimethyl acetal.

Original language	English (US)
Pages (from-to)	613-624
Number of pages	12
Journal	Nucleosides and Nucleotides
Volume	4
Issue number	5
DOIs	https://doi.org/10.1080/07328318508081894
State	Published - Dec 1 1985
Externally published	Yes

Bibliographical note

Funding Information:
1. This investigation was supported i n part by funds from the National Cancer Institute, D.H.H.S., Grants CA-08748 and CA-33907. 2. Pankiewicz, K. W.; Watanabe, K. A.; Takayanagi, H.; Itoh, T.; Ogura, H. J. Heterocyclic Chem., 1985, 3,0 000. 3. Pankiewicz, K.; Matsuda, A.; Watanabe, K. A. J. Org. Chem., 1982, -47, 475. 4. Markiewicz, W. T.; Biala, F.; Adamiak, R. W.; Grzeskowiak, K.; Kierzek, R.; Kraszewski, A.; Stawinski, J.; Wiewiorwski, M. Nucleic Acid Res. Symp. Ser. 1980, 1, 115. 5. Chu, C. K.; Reichman, U.; Watanabe, K. A.; Fox, J. J. J. Heterocyclic Chem., 1977, 14, 1119. 6. Greenberg, S.; Moffatt, J. G. J. Am. Chem. SOC., 1973, 2, 4016. 7. Reichman, U.; Chu, C. K.; Hollenberg, D. H.; Watanabe, K. A.; Fox, J. J. Synthesis, 1976, 533. Hanamura, E. K.; Prystas, M.; Verheyden, J. P. H.; Moffatt, J. G.; Yamaguchi, K.; Uehida, N.; Seto, K.; Nomura, A.; Shiratori, 0.; Takase, S.; Katagiri, K. J. Med. Chem.,1976,19,654. Akhren, A. A.; Zaitseva, G. V.; Mikhailopulo, I. A. Bioorg. Khim., 1976, 13, 1325. 8. Barton, D. J. R.; Subramanian, R. J. Chem. SOC., Chem. Commun., 1976, 863. J. Chem. SOC., Perkin Trans. L., 1977, 1718. 9. Robins, M. J.; Muhs,W. H. J. Chem. Soc.,Chem. Commun., 1978, 677. 10. Codington, J. F.; Doerr, I. L.; Fox, J. J. J. Org. Chem., 1964, -29, 558. 11. Reichman, U.; Chu, C. K.; Wempen, I.;Watanabe, K. A,; Fox, J. J. J. Heterocyclic Chem., 1976,13,933. Chu, C. K.; Reichman, U.; Watanabe, K. A.; Fox, J. J. J. Med. Chem., 1978,21, 96.

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Pankiewicz, K. W., & Watanabe, K. A. (1985). Nucleosides. 131. the Synthesis of 5-(2-Chloro-2-Deoxy-3-D-Arabino-Furanosyduracil. Reinterpretation of Reaction of ψ-Uridine with A-Acetoxyisobutyryl Chloride. Studies Directed Toward the Synthesis of 2¹-Deoxy-2¹-Substituted Arabinq-Nucleosides. 2. Nucleosides and Nucleotides, 4(5), 613-624. https://doi.org/10.1080/07328318508081894

Nucleosides. 131. the Synthesis of 5-(2-Chloro-2-Deoxy-3-D-Arabino-Furanosyduracil. Reinterpretation of Reaction of ψ-Uridine with A-Acetoxyisobutyryl Chloride. Studies Directed Toward the Synthesis of 2¹-Deoxy-2¹-Substituted Arabinq-Nucleosides. 2. / Pankiewicz, Krzysztof W.; Watanabe, Kyoichi A.
In: Nucleosides and Nucleotides, Vol. 4, No. 5, 01.12.1985, p. 613-624.

Research output: Contribution to journal › Article › peer-review

Pankiewicz, KW & Watanabe, KA 1985, 'Nucleosides. 131. the Synthesis of 5-(2-Chloro-2-Deoxy-3-D-Arabino-Furanosyduracil. Reinterpretation of Reaction of ψ-Uridine with A-Acetoxyisobutyryl Chloride. Studies Directed Toward the Synthesis of 2¹-Deoxy-2¹-Substituted Arabinq-Nucleosides. 2', Nucleosides and Nucleotides, vol. 4, no. 5, pp. 613-624. https://doi.org/10.1080/07328318508081894

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title = "Nucleosides. 131. the Synthesis of 5-(2-Chloro-2-Deoxy-3-D-Arabino-Furanosyduracil. Reinterpretation of Reaction of ψ-Uridine with A-Acetoxyisobutyryl Chloride. Studies Directed Toward the Synthesis of 21-Deoxy-21-Substituted Arabinq-Nucleosides. 2",

abstract = "Treatment of -uridine (3) with a-acetoxyisobutyryl chloride in acetonitrile gave, after deprotection, a mixture of four products: 5-(2-chloro-2-deoxy-B“D-arabinofuranosyljuracil (10a), its 3{\textquoteright}-chloro xylo isomer (11a), 2l-chloro-2'-deoxy--uridine (9a) and 4,2{\textquoteright}-anhydro--uridine (8a). Each component was isolated by column chromatography. Compound 9 was converted to the known 1,3-dimethyl derivative 2 by treatment with DMF-dimethylacetal. Treatment of 10 and 1_1 with NaOMe/MeOH afforded the same 4,2{\textquoteright}-anhydro-C-nucleoside 8. The 1,3-dimethyl analogues of TO and 11, however, were converted to 2{\textquoteleft},3{\textquoteright}-anhydro-l,3-dimethyl-i(j-uridine (13) upon base treatment. The epoxide 13 was also prepared in good yield by treatment of 10 and 11_ with DMF-dimethyl acetal.",

author = "Pankiewicz, {Krzysztof W.} and Watanabe, {Kyoichi A.}",

note = "Funding Information: 1. This investigation was supported i n part by funds from the National Cancer Institute, D.H.H.S., Grants CA-08748 and CA-33907. 2. Pankiewicz, K. W.; Watanabe, K. A.; Takayanagi, H.; Itoh, T.; Ogura, H. J. Heterocyclic Chem., 1985, 3,0 000. 3. Pankiewicz, K.; Matsuda, A.; Watanabe, K. A. J. Org. Chem., 1982, -47, 475. 4. Markiewicz, W. T.; Biala, F.; Adamiak, R. W.; Grzeskowiak, K.; Kierzek, R.; Kraszewski, A.; Stawinski, J.; Wiewiorwski, M. Nucleic Acid Res. Symp. Ser. 1980, 1, 115. 5. Chu, C. K.; Reichman, U.; Watanabe, K. A.; Fox, J. J. J. Heterocyclic Chem., 1977, 14, 1119. 6. Greenberg, S.; Moffatt, J. G. J. Am. Chem. SOC., 1973, 2, 4016. 7. Reichman, U.; Chu, C. K.; Hollenberg, D. H.; Watanabe, K. A.; Fox, J. J. Synthesis, 1976, 533. Hanamura, E. K.; Prystas, M.; Verheyden, J. P. H.; Moffatt, J. G.; Yamaguchi, K.; Uehida, N.; Seto, K.; Nomura, A.; Shiratori, 0.; Takase, S.; Katagiri, K. J. Med. Chem.,1976,19,654. Akhren, A. A.; Zaitseva, G. V.; Mikhailopulo, I. A. Bioorg. Khim., 1976, 13, 1325. 8. Barton, D. J. R.; Subramanian, R. J. Chem. SOC., Chem. Commun., 1976, 863. J. Chem. SOC., Perkin Trans. L., 1977, 1718. 9. Robins, M. J.; Muhs,W. H. J. Chem. Soc.,Chem. Commun., 1978, 677. 10. Codington, J. F.; Doerr, I. L.; Fox, J. J. J. Org. Chem., 1964, -29, 558. 11. Reichman, U.; Chu, C. K.; Wempen, I.;Watanabe, K. A,; Fox, J. J. J. Heterocyclic Chem., 1976,13,933. Chu, C. K.; Reichman, U.; Watanabe, K. A.; Fox, J. J. J. Med. Chem., 1978,21, 96.",

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T1 - Nucleosides. 131. the Synthesis of 5-(2-Chloro-2-Deoxy-3-D-Arabino-Furanosyduracil. Reinterpretation of Reaction of ψ-Uridine with A-Acetoxyisobutyryl Chloride. Studies Directed Toward the Synthesis of 21-Deoxy-21-Substituted Arabinq-Nucleosides. 2

AU - Pankiewicz, Krzysztof W.

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N1 - Funding Information: 1. This investigation was supported i n part by funds from the National Cancer Institute, D.H.H.S., Grants CA-08748 and CA-33907. 2. Pankiewicz, K. W.; Watanabe, K. A.; Takayanagi, H.; Itoh, T.; Ogura, H. J. Heterocyclic Chem., 1985, 3,0 000. 3. Pankiewicz, K.; Matsuda, A.; Watanabe, K. A. J. Org. Chem., 1982, -47, 475. 4. Markiewicz, W. T.; Biala, F.; Adamiak, R. W.; Grzeskowiak, K.; Kierzek, R.; Kraszewski, A.; Stawinski, J.; Wiewiorwski, M. Nucleic Acid Res. Symp. Ser. 1980, 1, 115. 5. Chu, C. K.; Reichman, U.; Watanabe, K. A.; Fox, J. J. J. Heterocyclic Chem., 1977, 14, 1119. 6. Greenberg, S.; Moffatt, J. G. J. Am. Chem. SOC., 1973, 2, 4016. 7. Reichman, U.; Chu, C. K.; Hollenberg, D. H.; Watanabe, K. A.; Fox, J. J. Synthesis, 1976, 533. Hanamura, E. K.; Prystas, M.; Verheyden, J. P. H.; Moffatt, J. G.; Yamaguchi, K.; Uehida, N.; Seto, K.; Nomura, A.; Shiratori, 0.; Takase, S.; Katagiri, K. J. Med. Chem.,1976,19,654. Akhren, A. A.; Zaitseva, G. V.; Mikhailopulo, I. A. Bioorg. Khim., 1976, 13, 1325. 8. Barton, D. J. R.; Subramanian, R. J. Chem. SOC., Chem. Commun., 1976, 863. J. Chem. SOC., Perkin Trans. L., 1977, 1718. 9. Robins, M. J.; Muhs,W. H. J. Chem. Soc.,Chem. Commun., 1978, 677. 10. Codington, J. F.; Doerr, I. L.; Fox, J. J. J. Org. Chem., 1964, -29, 558. 11. Reichman, U.; Chu, C. K.; Wempen, I.;Watanabe, K. A,; Fox, J. J. J. Heterocyclic Chem., 1976,13,933. Chu, C. K.; Reichman, U.; Watanabe, K. A.; Fox, J. J. J. Med. Chem., 1978,21, 96.

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N2 - Treatment of -uridine (3) with a-acetoxyisobutyryl chloride in acetonitrile gave, after deprotection, a mixture of four products: 5-(2-chloro-2-deoxy-B“D-arabinofuranosyljuracil (10a), its 3’-chloro xylo isomer (11a), 2l-chloro-2'-deoxy--uridine (9a) and 4,2’-anhydro--uridine (8a). Each component was isolated by column chromatography. Compound 9 was converted to the known 1,3-dimethyl derivative 2 by treatment with DMF-dimethylacetal. Treatment of 10 and 1_1 with NaOMe/MeOH afforded the same 4,2’-anhydro-C-nucleoside 8. The 1,3-dimethyl analogues of TO and 11, however, were converted to 2‘,3’-anhydro-l,3-dimethyl-i(j-uridine (13) upon base treatment. The epoxide 13 was also prepared in good yield by treatment of 10 and 11_ with DMF-dimethyl acetal.

AB - Treatment of -uridine (3) with a-acetoxyisobutyryl chloride in acetonitrile gave, after deprotection, a mixture of four products: 5-(2-chloro-2-deoxy-B“D-arabinofuranosyljuracil (10a), its 3’-chloro xylo isomer (11a), 2l-chloro-2'-deoxy--uridine (9a) and 4,2’-anhydro--uridine (8a). Each component was isolated by column chromatography. Compound 9 was converted to the known 1,3-dimethyl derivative 2 by treatment with DMF-dimethylacetal. Treatment of 10 and 1_1 with NaOMe/MeOH afforded the same 4,2’-anhydro-C-nucleoside 8. The 1,3-dimethyl analogues of TO and 11, however, were converted to 2‘,3’-anhydro-l,3-dimethyl-i(j-uridine (13) upon base treatment. The epoxide 13 was also prepared in good yield by treatment of 10 and 11_ with DMF-dimethyl acetal.

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