Stereoselective route to a new class of phosphasugars. Novel analogues of 2-deoxyglucose and 2-deoxyallose

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 436-437

  Gallagher, Michael J ^a   Ranasinghe, Millagahamada G ^a   Jenkins, Ian D ^b  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

^b GRIFFITH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

3 PHOSPHASUGAR; CARBOHYDRATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030058154     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951479u     Document Type: Article

References (16)

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2. Yamomoto, H.; Inokawa, S, Adv. Carbohydr. Chem. Biochem. 1984, 42, 130-91. Darrow, J. W.; Druekhammer, D. G. J. Org. Chem. 1994, 59, 2976. Hanya, T.; Yasuda, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 2315. Dessinges, A ; Vasella, A. Carbohydr. Res. 1988, 174, 47. Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. Chem. Lett. 1989, 121 Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. J. Org. Chem. 1988, 53, 4790. Seo, K.; Yamashita, M. Carbohydr. Res. 1986, 148, 168. Wroblewski, A. E. Z. Naturforsch. B 1986, 40B, 791. Bodalski, R.; Tomasz, J. Bull. Pol. Acad. Sci. Chem. 1988, 35, 529.
3. Yamomoto, H.; Inokawa, S, Adv. Carbohydr. Chem. Biochem. 1984, 42, 130-91. Darrow, J. W.; Druekhammer, D. G. J. Org. Chem. 1994, 59, 2976. Hanya, T.; Yasuda, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 2315. Dessinges, A ; Vasella, A. Carbohydr. Res. 1988, 174, 47. Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. Chem. Lett. 1989, 121 Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. J. Org. Chem. 1988, 53, 4790. Seo, K.; Yamashita, M. Carbohydr. Res. 1986, 148, 168. Wroblewski, A. E. Z. Naturforsch. B 1986, 40B, 791. Bodalski, R.; Tomasz, J. Bull. Pol. Acad. Sci. Chem. 1988, 35, 529.
4. Yamomoto, H.; Inokawa, S, Adv. Carbohydr. Chem. Biochem. 1984, 42, 130-91. Darrow, J. W.; Druekhammer, D. G. J. Org. Chem. 1994, 59, 2976. Hanya, T.; Yasuda, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 2315. Dessinges, A ; Vasella, A. Carbohydr. Res. 1988, 174, 47. Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. Chem. Lett. 1989, 121 Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. J. Org. Chem. 1988, 53, 4790. Seo, K.; Yamashita, M. Carbohydr. Res. 1986, 148, 168. Wroblewski, A. E. Z. Naturforsch. B 1986, 40B, 791. Bodalski, R.; Tomasz, J. Bull. Pol. Acad. Sci. Chem. 1988, 35, 529.
5. Yamomoto, H.; Inokawa, S, Adv. Carbohydr. Chem. Biochem. 1984, 42, 130-91. Darrow, J. W.; Druekhammer, D. G. J. Org. Chem. 1994, 59, 2976. Hanya, T.; Yasuda, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 2315. Dessinges, A ; Vasella, A. Carbohydr. Res. 1988, 174, 47. Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. Chem. Lett. 1989, 121 Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. J. Org. Chem. 1988, 53, 4790. Seo, K.; Yamashita, M. Carbohydr. Res. 1986, 148, 168. Wroblewski, A. E. Z. Naturforsch. B 1986, 40B, 791. Bodalski, R.; Tomasz, J. Bull. Pol. Acad. Sci. Chem. 1988, 35, 529.
6. Yamomoto, H.; Inokawa, S, Adv. Carbohydr. Chem. Biochem. 1984, 42, 130-91. Darrow, J. W.; Druekhammer, D. G. J. Org. Chem. 1994, 59, 2976. Hanya, T.; Yasuda, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 2315. Dessinges, A ; Vasella, A. Carbohydr. Res. 1988, 174, 47. Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. Chem. Lett. 1989, 121 Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. J. Org. Chem. 1988, 53, 4790. Seo, K.; Yamashita, M. Carbohydr. Res. 1986, 148, 168. Wroblewski, A. E. Z. Naturforsch. B 1986, 40B, 791. Bodalski, R.; Tomasz, J. Bull. Pol. Acad. Sci. Chem. 1988, 35, 529.
7. Yamomoto, H.; Inokawa, S, Adv. Carbohydr. Chem. Biochem. 1984, 42, 130-91. Darrow, J. W.; Druekhammer, D. G. J. Org. Chem. 1994, 59, 2976. Hanya, T.; Yasuda, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 2315. Dessinges, A ; Vasella, A. Carbohydr. Res. 1988, 174, 47. Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. Chem. Lett. 1989, 121 Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. J. Org. Chem. 1988, 53, 4790. Seo, K.; Yamashita, M. Carbohydr. Res. 1986, 148, 168. Wroblewski, A. E. Z. Naturforsch. B 1986, 40B, 791. Bodalski, R.; Tomasz, J. Bull. Pol. Acad. Sci. Chem. 1988, 35, 529.
8. Yamomoto, H.; Inokawa, S, Adv. Carbohydr. Chem. Biochem. 1984, 42, 130-91. Darrow, J. W.; Druekhammer, D. G. J. Org. Chem. 1994, 59, 2976. Hanya, T.; Yasuda, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 2315. Dessinges, A ; Vasella, A. Carbohydr. Res. 1988, 174, 47. Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. Chem. Lett. 1989, 121 Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. J. Org. Chem. 1988, 53, 4790. Seo, K.; Yamashita, M. Carbohydr. Res. 1986, 148, 168. Wroblewski, A. E. Z. Naturforsch. B 1986, 40B, 791. Bodalski, R.; Tomasz, J. Bull. Pol. Acad. Sci. Chem. 1988, 35, 529.
9. Yamomoto, H.; Inokawa, S, Adv. Carbohydr. Chem. Biochem. 1984, 42, 130-91. Darrow, J. W.; Druekhammer, D. G. J. Org. Chem. 1994, 59, 2976. Hanya, T.; Yasuda, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 2315. Dessinges, A ; Vasella, A. Carbohydr. Res. 1988, 174, 47. Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. Chem. Lett. 1989, 121 Yamoto, H.; Hanya, T.; Kawamoto, H.; Inokawa, S. J. Org. Chem. 1988, 53, 4790. Seo, K.; Yamashita, M. Carbohydr. Res. 1986, 148, 168. Wroblewski, A. E. Z. Naturforsch. B 1986, 40B, 791. Bodalski, R.; Tomasz, J. Bull. Pol. Acad. Sci. Chem. 1988, 35, 529.
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11. Gallagher, M. J.; Ranasinghe, M. G. Abstract, 14th RACI Natl. Org. Conf. Wollongong, Australia, 1994, p P77.
12. Fookes, C. J.; Gallagher, M. J. In Biophosphates and Their Analogues; Brucizk, K. S., Stec, W., Eds.; Elsevier: Amsterdam, 1987; pp 233-234.
13. 2) suggest that the reaction is controlled by both the ready reversibility of the addition and the bulk of the silane. We will report on a detailed study of these factors at a later date.
14. 1 would be expected with the resultant predominant formation of the less hindered equatorial acetate. The enol acetate formation presumably occurs with the acyclic form since 5a,b are stable under the acetylation conditions.
15. 9P: C, 45.88; H, 6.33; found: C, 45.63; H, 6.48.
16. Craig, D. C.; Gallagher, M. J.; Jenkins, I. D.; Ranasinghe, M. G. To be published.