A short and efficient synthesis of 1,5-dideoxy-1,5-imino-D-galactitol (1-deoxy-D-galactostatin) and 1,5-dideoxy-1,5-imino-L-altritol (1-deoxy-L- altrostatin) from D-galactose

Synlett

Volumn , Issue 5, 1999, Pages 593-595

  Uriel, Clara ^a   Santoyo González, Francisco ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

Altrostatin; Azasugars; Galactose; Galactostatin; Triflation

Indexed keywords

1 DEOXY LEVO ALTROSTATIN; 1 DEOXYGALACTOSTATIN; CARBOHYDRATE DERIVATIVE; GALACTOSE; GALACTOSIDASE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; STRUCTURE ANALYSIS;

EID: 0032930959     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3158     Document Type: Article

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31. 3), 4.11 (dd, 1H, J = 13.1 and J = 6.6 Hz, H-6), 4.30 (t, 1 H, J = 7.2 Hz, H-4), 4.53 (dd, 1 H, H = 13.1 and 2.8 Hz, H-6′), 5.14 (m, 1 H, H-5), 5.46 (dd, 1 H, J = 7.2 and 4.3 Hz, H-2), 5.55 (t, 1 H, J = 7.2 Hz, H-3), 6.40 (d, 1 H, J = 4.3 Hz, H-I)
32. 9: C, 57.64; H, 8.01. Found: C, 57.88; H, 8.27.
33. 2O, 300MHz): δ 63.4 (C-6), 66.9, 67.9, 77.4, 78.7, 82.0, 83.9, 84.5 (C-2,3,4,5), 97.9, 103.6 (C-1).
34. 2O, 300 MHz): δ 59.9 (C-5), 62.0, 65.4 (C-1, 6), 70.9, 71.5 (C-3,4), 99.8 (C-2).
35. 2O, 300 MHz): δ 44.6 (C-1), 55.9 (C-5), 60.2 (C-6), 65.5 (C-4), 68.6 (C-2), 70.2 (C-3).
36. 10Na: 539.2832, found: 539.2830
37. 3), 4.26 (dd, 1 H, J = 13.2 and 6.6 Hz, H-6), 4.34 (t, 1 H, J = 7.2 Hz, H-4), 4.56 (dd, 1 H, J = 2.3 Hz, H-6), 5.23 (m, I H, H-5), 5.44 (dd, 1 H, J = 7.2 and 4.4 Hz, H-2), 5.54 (t, 1 H, J = 7.2 Hz, H-3), 6.38 (d, 1 H, J = 4.4 Hz, H-1)
38. 9 C, 57.64; H, 8.01; N, 7.76. Found: C, 57.41 ;H, 8.39; N, 7.52.
39. 2O): δ 62.4, 63.0 (C-6), 65.1, 66.7, 76.6, 77.6, 78.1, 81.5, 82.8, 82.9 (C-2,3,4,5), 96.8, 102.5 (C-1)
40. 2O): 49.1 (C-1), 61.5 (C-6), 59.2, 68.2, 69.3, 75.2 (C-2,3,4,5).