A stereoselective synthesis of methyl β-C-lactoside through the tether approach

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3697-3700

  Rubinstenn, Gilles ^a   Mallet, Jean Maurice ^a   Sinaÿ, Pierre ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LACTOSE; PYRANOSIDE;

ARTICLE; CYCLIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032575153     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00649-2     Document Type: Article

References (40)

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29. 3d. This compound has also been converted classically into methyl β-C-lactoside, see 4d.
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34. 2,3 8.5Hz, H-3), 3.66 (ddd, 1H, H-5), 3.59 (s, 3H, OMe), 3.48 (dd, 1H, H-2), 2.52 (s, 1H, OH), 0.95 (s, 9H, tBuSi), 0.14 (s, 3H, MeSi), 0.11 (s, 3H, MeSi).
35. 2,3 7.5Hz, H-2).
36. 6d.
37. 3CO).
38. 2O, 298K) : 104.42 (C-1), 79.71 (C-5'), 78.22 (C-5), 78.84 (C-1'), 75.92 (C-2), 75.18 (C-3'), 74.95 (C-3), 72.46 (C-2'), 70.44 (C-4'), 63.25 (C-6), 62.83 (C-6'), 58.23 (C-OMe), 41.69 (C-4), 29.61 (C-4h).
39. 6 a stereoselective reduction of the C-4 generated radical from the β side to give a gluco moiety.
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