Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry v. synthesis of 1,2-trans-linked 1-thioglycosides from the per-o-acetylated glycoses

Journal of Carbohydrate Chemistry

Volumn 17, Issue 4-5, 1998, Pages 693-702

  Kartha, K P Ravindranathan ^a   Field, Robert A ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007829465     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309808002346     Document Type: Article

References (17)

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3. V. Pozsgay and H. J. Jennings, Tetrahedron Lett., 28, 1375 (1987) and references 8 to 11 cited therein; R. J. Ferrier and R.H. Furneaux, Carbohydr. Res., 52, 63 (1976).
4. M. R. Detty, Tetrahedron Lett., 4189 (1979);
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7. J. A. Kerr in CRC Handbook of Chemistry and Physics, D. R. Lide, Ed.; CRC Press: Boca Raton, 1991, pp 9-117.
8. 1H FT NMR Spectra, 1(1), 425b
9. T-L. Ho and G. A. Olah, Proc. Natl. Acad. Sci. USA, 75, 4 (1978); G. A. Olah, S. C. Narang, B. G. B. Gupta and R. Malhotra, J. Org. Chem., 44, 1247 (1979); G. A. Olah, S. C. Narang, B. G. B. Gupta and R. Malhotra, Angew. Chem. Int. Ed. Engl., 612 (1979).
10. T-L. Ho and G. A. Olah, Proc. Natl. Acad. Sci. USA, 75, 4 (1978); G. A. Olah, S. C. Narang, B. G. B. Gupta and R. Malhotra, J. Org. Chem., 44, 1247 (1979); G. A. Olah, S. C. Narang, B. G. B. Gupta and R. Malhotra, Angew. Chem. Int. Ed. Engl., 612 (1979).
11. T-L. Ho and G. A. Olah, Proc. Natl. Acad. Sci. USA, 75, 4 (1978); G. A. Olah, S. C. Narang, B. G. B. Gupta and R. Malhotra, J. Org. Chem., 44, 1247 (1979); G. A. Olah, S. C. Narang, B. G. B. Gupta and R. Malhotra, Angew. Chem. Int. Ed. Engl., 612 (1979).
12. K. P. R. Kartha and R. A. Field, Tetrahadron Lett., 38, 8233 (1997); K. P. R. Kartha, M. Aloui and R. A. Field, Tetrahedron Lett., 37, 5175 (1996).
13. K. P. R. Kartha and R. A. Field, Tetrahadron Lett., 38, 8233 (1997); K. P. R. Kartha, M. Aloui and R. A. Field, Tetrahedron Lett., 37, 5175 (1996).
14. 3CN (0.8 mL) containing 2 (78.1 mg, 0.2 mmol).The dark brown solution thus obtained was cooled to about 10°C (or below as desired) and 1/TMS-SEt (1.2 mol equiv) was added to it. After mixing the reagents well the reaction was monitored by NMR.
15. J. Thiem and B. Meyer, Chem. Ber., 113, 3075 (1980).
16. In general, reactions involving TMSSPh, TMSSEt and EtSH were found more prone to giving the by-product (1,2-cis-1-thioglycoside) than those involving 1, possibly because the thiolates derived from the former reagents are harder nucleophiles.
17. J. Fried and D, E. Walz, J. Am. Chem. Soc., 71, 140 (1949).