Stereoselective synthesis of the α-glucosidase inhibitor nectrisine

Tetrahedron Letters

Volumn 44, Issue 41, 2003, Pages 7649-7653

  Hulme, Alison N ^a   Montgomery, Charles H ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

Glycolate aldol; Glycosidase inhibitors; Iminosugars

Indexed keywords

ALPHA GLUCOSIDASE INHIBITOR; CARBOHYDRATE DERIVATIVE; FR 9000483; GLYCOLIC ACID; NECTRISINE; SERINE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0141852863     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.030     Document Type: Article

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46. Compound 6 was unambiguously determined as the all-syn product by single crystal X-ray diffraction.
47. 3) 174.3, 139.3 (2C), 135.6 (2C), 135.5 (2C), 132.6, 132.5, 129.9 (2C), 128.9 (4C), 128.2 (4C), 127.8 (4C), 127.0 (2C), 72.4, 70.5, 61.5, 58.7, 54.9 (2C), 52.3, 26.7 (3C), 18.9.
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50. Synthesized via reaction of the sodium salt of benzyl alcohol with bromoacetic acid, followed by esterification.
51. 3) 172.3, 140.0 (2C), 137.4, 135.6 (2C), 135.5 (2C), 133.1, 132.9, 129.7, 129.6, 129.2 (4C), 128.2 (4C), 127.9 (4C), 127.6 (4C), 127.5, 126.9 (2C), 77.3, 72.8, 72.1, 61.2, 59.1, 54.8 (2C), 51.8, 26.7 (3C), 18.9.
52. 3) 176.6, 135.4 (4C), 132.6, 129.9 (2C), 127.8 (4C), 76.9, 65.1, 61.2 (2C), 44.9, 16.7 (3C), 19.0, 13.0.
53. 3) 171.7, 153.1, 140.0 (2C), 137.4, 135.7 (2C), 135.6 (2C), 135.0, 133.1, 133.0, 129.7 (2C), 129.3 (2C), 129.1 (4C), 128.8 (2C), 128.1 (2C), 128.0 (4C), 127.9 (2C), 127.7 (4C), 127.5, 127.2, 126.7 (2C), 78.3, 72.2, 72.0, 66.7, 61.5, 59.7, 54.7 (3C), 37.7, 26.7 (3C), 18.9.
54. 3) 175.4, 135.5 (2C), 135.4 (2C), 132.6, 132.4, 129.8, 129.8, 127.8 (4C), 74.9 (2C), 62.6, 55.5, 26.7 (3C), 18.9.
55. For recent examples of the use of this strategy see: (a) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029-4032; (b) Mulzer, J.; Schülzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298; (c) Oba, M.; Miyakawa, A.; Nishiyama, K. J. Org. Chem. 1999, 46, 9275-9278; (d) Langlois, N. Tetrahedron: Asymmetry 1998, 9, 1333-1336.
56. For recent examples of the use of this strategy see: (a) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029-4032; (b) Mulzer, J.; Schülzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298; (c) Oba, M.; Miyakawa, A.; Nishiyama, K. J. Org. Chem. 1999, 46, 9275-9278; (d) Langlois, N. Tetrahedron: Asymmetry 1998, 9, 1333-1336.
57. For recent examples of the use of this strategy see: (a) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029-4032; (b) Mulzer, J.; Schülzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298; (c) Oba, M.; Miyakawa, A.; Nishiyama, K. J. Org. Chem. 1999, 46, 9275-9278; (d) Langlois, N. Tetrahedron: Asymmetry 1998, 9, 1333-1336.
58. For recent examples of the use of this strategy see: (a) Zhang, J.; Xiong, C.; Wang, W.; Ying, J.; Hruby, V. J. Org. Lett. 2002, 4, 4029-4032; (b) Mulzer, J.; Schülzchen, F.; Bats, J.-W. Tetrahedron 2000, 56, 4289-4298; (c) Oba, M.; Miyakawa, A.; Nishiyama, K. J. Org. Chem. 1999, 46, 9275-9278; (d) Langlois, N. Tetrahedron: Asymmetry 1998, 9, 1333-1336.
59. 3) 175.5, 149.8, 135.5 (4C), 132.8, 132.5, 129.8 (2C), 127.7 (4C), 82.8, 72.7, 66.8, 62.0, 47.8, 27.8 (3C), 26.8 (3C), 25.5 (3C), 19.1, 17.7, 14.5, -4.5, -4.7.
60. 3 requires 131.0582, found 131.0582).