Further studies in α-C-mannosylation promoted by samarium diiodide

Tetrahedron Letters

Volumn 38, Issue 10, 1997, Pages 1767-1770

  Jarreton, Olivier ^a   Skrydstrup, Troels ^a   Beau, Jean Marie ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE; MANNOSIDE; SAMARIUM;

ARTICLE; CARBOHYDRATE SYNTHESIS; CONFORMATIONAL TRANSITION; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0031562391     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00206-2     Document Type: Article

References (15)

1. 1. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem. Int. Ed. Engl. 1995, 34, 909-912.
2. 2. Jarreton, O.; Skrydstrup, T.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1661-1662. For a recent example for the synthesis of other C-glycosides employing this approach, see, Urban, D.; Skrydstmp, T.; Riche, C.; Chiaroni, A.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1883-1884.
3. 2. Jarreton, O.; Skrydstrup, T.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1661-1662. For a recent example for the synthesis of other C-glycosides employing this approach, see, Urban, D.; Skrydstmp, T.; Riche, C.; Chiaroni, A.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1883-1884.
4. 3. Lancelin, J.-M.; Morin-Allory, L.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1984, 355-356.
5. 4. Pedretti, A.; Veyrières, A.; Sinaÿ, P. Tetrahedron 1990, 46, 77-88.
6. 5. In the gluco-case, deprotonation of the C2-OH prior to lithiation can lead to a stable anomeric lithium species at low temperature: a) Wittmann, V.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1993, 32, 1091-1093;
7. b) Lesimple, P.; Beau, J.-M. Bioorg. Med. Chem. 1994, 2, 1319-1330.
8. 6. Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem. Int. Ed. Engl. 1994, 33, 1383-1386. Skrydstrup, T.; Mazéas, D.; Elmouchir, M.; Riche, C.; Chiaroni, A.; Doisneau, G.; Beau, J.-M. submitted for publication.
9. 6. Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem. Int. Ed. Engl. 1994, 33, 1383-1386. Skrydstrup, T.; Mazéas, D.; Elmouchir, M.; Riche, C.; Chiaroni, A.; Doisneau, G.; Beau, J.-M. submitted for publication.
10. III metal ion which facilitates elimination. This is probably the case for entries 6 and 7 as well. Internal coordination through a four-membered ring chelate with a C2-alkoxide may explain the preference for β-C-mannoside formation in entry 8.
11. 2, and the organic phase was dried and evaporated to dryness. The crude product was purified by flash chromatography.
12. 9. Rychnovsky, S.D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515. Richardson, T.I., Rychnovsky, S.D. J. Org. Chem. 1996, 61, 4219-4231.
13. 9. Rychnovsky, S.D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515. Richardson, T.I., Rychnovsky, S.D. J. Org. Chem. 1996, 61, 4219-4231.
14. 3).
15. 11. Hung, S.-C; Wong, C.-H. Tetrahedron Lett. 1996, 37, 4903-4906.