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Volumn 338, Issue 21, 2003, Pages 2237-2240

A mild and convenient indium(III) chloride-catalyzed synthesis of thioglycosides

Author keywords

Indium(III) chloride; Stereoselectivity; Thioglycoside; Thiols

Indexed keywords

CATALYST ACTIVITY; CATALYST SELECTIVITY; INDIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 1542399532     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00355-0     Document Type: Article
Times cited : (43)

References (30)
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    • For some widely used methods see: (a) Fried, J.; Walz, D. E. J. Am. Chem. Soc. 1949, 71, 140-143; (b) Kihlberg, J. O.; Leigh, D. A.; Bundle, D. R. J. Org. Chem. 1990, 55, 2860-2863; (c) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172; (d) Das, S. K.; Roy, N. Carbohydr. Res. 1996, 296, 275-277; (e) Lemieux, R. U. Can. J. Chem. 1951, 29, 1079-1091; (f) Nakano, T.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1993, 243, 43-70; (g) Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Carbohydr. Res. 1995, 275, 179-184; (h) Pozsgay, V.; Jennings, H. J. Tetrahedron Lett. 1987, 28, 1375-1376; (i) Singh, S.; Scigelova, M.; Critchley, P.; Crout, D. H. G. Carbohydr. Res. 1998, 305, 363-370; (j) Lönn, H. Carbohydr. Res. 1985, 139, 105-114; (k) Dasgupta, F. ; Garegg, P. J. Acta Chem. Scand. 1989, 43, 471-475.
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    • Kihlberg, J.O.1    Leigh, D.A.2    Bundle, D.R.3
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    • For some widely used methods see: (a) Fried, J.; Walz, D. E. J. Am. Chem. Soc. 1949, 71, 140-143; (b) Kihlberg, J. O.; Leigh, D. A.; Bundle, D. R. J. Org. Chem. 1990, 55, 2860-2863; (c) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172; (d) Das, S. K.; Roy, N. Carbohydr. Res. 1996, 296, 275-277; (e) Lemieux, R. U. Can. J. Chem. 1951, 29, 1079-1091; (f) Nakano, T.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1993, 243, 43-70; (g) Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Carbohydr. Res. 1995, 275, 179-184; (h) Pozsgay, V.; Jennings, H. J. Tetrahedron Lett. 1987, 28, 1375-1376; (i) Singh, S.; Scigelova, M.; Critchley, P.; Crout, D. H. G. Carbohydr. Res. 1998, 305, 363-370; (j) Lönn, H. Carbohydr. Res. 1985, 139, 105-114; (k) Dasgupta, F. ; Garegg, P. J. Acta Chem. Scand. 1989, 43, 471-475.
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    • Nilsson, M.1    Svahn, C.-M.2    Westman, J.3
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    • For some widely used methods see: (a) Fried, J.; Walz, D. E. J. Am. Chem. Soc. 1949, 71, 140-143; (b) Kihlberg, J. O.; Leigh, D. A.; Bundle, D. R. J. Org. Chem. 1990, 55, 2860-2863; (c) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172; (d) Das, S. K.; Roy, N. Carbohydr. Res. 1996, 296, 275-277; (e) Lemieux, R. U. Can. J. Chem. 1951, 29, 1079-1091; (f) Nakano, T.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1993, 243, 43-70; (g) Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Carbohydr. Res. 1995, 275, 179-184; (h) Pozsgay, V.; Jennings, H. J. Tetrahedron Lett. 1987, 28, 1375-1376; (i) Singh, S.; Scigelova, M.; Critchley, P.; Crout, D. H. G. Carbohydr. Res. 1998, 305, 363-370; (j) Lönn, H. Carbohydr. Res. 1985, 139, 105-114; (k) Dasgupta, F. ; Garegg, P. J. Acta Chem. Scand. 1989, 43, 471-475.
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    • Nakano, T.1    Ito, Y.2    Ogawa, T.3
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    • For some widely used methods see: (a) Fried, J.; Walz, D. E. J. Am. Chem. Soc. 1949, 71, 140-143; (b) Kihlberg, J. O.; Leigh, D. A.; Bundle, D. R. J. Org. Chem. 1990, 55, 2860-2863; (c) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172; (d) Das, S. K.; Roy, N. Carbohydr. Res. 1996, 296, 275-277; (e) Lemieux, R. U. Can. J. Chem. 1951, 29, 1079-1091; (f) Nakano, T.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1993, 243, 43-70; (g) Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Carbohydr. Res. 1995, 275, 179-184; (h) Pozsgay, V.; Jennings, H. J. Tetrahedron Lett. 1987, 28, 1375-1376; (i) Singh, S.; Scigelova, M.; Critchley, P.; Crout, D. H. G. Carbohydr. Res. 1998, 305, 363-370; (j) Lönn, H. Carbohydr. Res. 1985, 139, 105-114; (k) Dasgupta, F. ; Garegg, P. J. Acta Chem. Scand. 1989, 43, 471-475.
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    • Li, P.1    Sun, L.2    Landry, D.W.3    Zhao, K.4
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    • 0001574318 scopus 로고
    • For some widely used methods see: (a) Fried, J.; Walz, D. E. J. Am. Chem. Soc. 1949, 71, 140-143; (b) Kihlberg, J. O.; Leigh, D. A.; Bundle, D. R. J. Org. Chem. 1990, 55, 2860-2863; (c) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172; (d) Das, S. K.; Roy, N. Carbohydr. Res. 1996, 296, 275-277; (e) Lemieux, R. U. Can. J. Chem. 1951, 29, 1079-1091; (f) Nakano, T.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1993, 243, 43-70; (g) Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Carbohydr. Res. 1995, 275, 179-184; (h) Pozsgay, V.; Jennings, H. J. Tetrahedron Lett. 1987, 28, 1375-1376; (i) Singh, S.; Scigelova, M.; Critchley, P.; Crout, D. H. G. Carbohydr. Res. 1998, 305, 363-370; (j) Lönn, H. Carbohydr. Res. 1985, 139, 105-114; (k) Dasgupta, F. ; Garegg, P. J. Acta Chem. Scand. 1989, 43, 471-475.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 1375-1376
    • Pozsgay, V.1    Jennings, H.J.2
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    • 0031395398 scopus 로고    scopus 로고
    • For some widely used methods see: (a) Fried, J.; Walz, D. E. J. Am. Chem. Soc. 1949, 71, 140-143; (b) Kihlberg, J. O.; Leigh, D. A.; Bundle, D. R. J. Org. Chem. 1990, 55, 2860-2863; (c) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172; (d) Das, S. K.; Roy, N. Carbohydr. Res. 1996, 296, 275-277; (e) Lemieux, R. U. Can. J. Chem. 1951, 29, 1079-1091; (f) Nakano, T.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1993, 243, 43-70; (g) Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Carbohydr. Res. 1995, 275, 179-184; (h) Pozsgay, V.; Jennings, H. J. Tetrahedron Lett. 1987, 28, 1375-1376; (i) Singh, S.; Scigelova, M.; Critchley, P.; Crout, D. H. G. Carbohydr. Res. 1998, 305, 363-370; (j) Lönn, H. Carbohydr. Res. 1985, 139, 105-114; (k) Dasgupta, F. ; Garegg, P. J. Acta Chem. Scand. 1989, 43, 471-475.
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    • Singh, S.1    Scigelova, M.2    Critchley, P.3    Crout, D.H.G.4
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    • 0022426354 scopus 로고
    • For some widely used methods see: (a) Fried, J.; Walz, D. E. J. Am. Chem. Soc. 1949, 71, 140-143; (b) Kihlberg, J. O.; Leigh, D. A.; Bundle, D. R. J. Org. Chem. 1990, 55, 2860-2863; (c) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172; (d) Das, S. K.; Roy, N. Carbohydr. Res. 1996, 296, 275-277; (e) Lemieux, R. U. Can. J. Chem. 1951, 29, 1079-1091; (f) Nakano, T.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1993, 243, 43-70; (g) Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Carbohydr. Res. 1995, 275, 179-184; (h) Pozsgay, V.; Jennings, H. J. Tetrahedron Lett. 1987, 28, 1375-1376; (i) Singh, S.; Scigelova, M.; Critchley, P.; Crout, D. H. G. Carbohydr. Res. 1998, 305, 363-370; (j) Lönn, H. Carbohydr. Res. 1985, 139, 105-114; (k) Dasgupta, F. ; Garegg, P. J. Acta Chem. Scand. 1989, 43, 471-475.
    • (1985) Carbohydr. Res. , vol.139 , pp. 105-114
    • Lönn, H.1
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    • 0001591142 scopus 로고
    • For some widely used methods see: (a) Fried, J.; Walz, D. E. J. Am. Chem. Soc. 1949, 71, 140-143; (b) Kihlberg, J. O.; Leigh, D. A.; Bundle, D. R. J. Org. Chem. 1990, 55, 2860-2863; (c) Nilsson, M.; Svahn, C.-M.; Westman, J. Carbohydr. Res. 1993, 246, 161-172; (d) Das, S. K.; Roy, N. Carbohydr. Res. 1996, 296, 275-277; (e) Lemieux, R. U. Can. J. Chem. 1951, 29, 1079-1091; (f) Nakano, T.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1993, 243, 43-70; (g) Li, P.; Sun, L.; Landry, D. W.; Zhao, K. Carbohydr. Res. 1995, 275, 179-184; (h) Pozsgay, V.; Jennings, H. J. Tetrahedron Lett. 1987, 28, 1375-1376; (i) Singh, S.; Scigelova, M.; Critchley, P.; Crout, D. H. G. Carbohydr. Res. 1998, 305, 363-370; (j) Lönn, H. Carbohydr. Res. 1985, 139, 105-114; (k) Dasgupta, F. ; Garegg, P. J. Acta Chem. Scand. 1989, 43, 471-475.
    • (1989) Acta Chem. Scand. , vol.43 , pp. 471-475
    • Dasgupta, F.1    Garegg, P.J.2
  • 13
    • 0033928629 scopus 로고    scopus 로고
    • and references therein;
    • For review see: (a) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347-2356 and references therein; (b) Ghosh, R. Indian J. Chem. 2001, 40B, 550-557 and references therein.
    • (2000) Eur. J. Org. Chem. , pp. 2347-2356
    • Ranu, B.C.1
  • 14
    • 0034896418 scopus 로고    scopus 로고
    • and references therein.
    • For review see: (a) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347-2356 and references therein; (b) Ghosh, R. Indian J. Chem. 2001, 40B, 550-557 and references therein.
    • (2001) Indian J. Chem. , vol.40 B , pp. 550-557
    • Ghosh, R.1


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