A novel and expeditious approach to the stereoselective synthesis of 2- S-ethyl(phenyl)-2-deoxy-β-glycosides, ready precursors to 2-deoxy-β- glycosides

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2961-2964

  Yu, Biao ^a   Yang, Zunyi ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; METHODOLOGY; STRUCTURE ANALYSIS;

EID: 0034656158     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00281-1     Document Type: Article

References (15)

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2. For reviews, see: (a) Boons, G.-J. Contemporary Organic Synthesis 1996, 173.
3. (b) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
4. For the latest successful examples, see: (a) Roush, W. R.; Gung, B. W.; Bennett, C. E. Org. Lett. 1999, 1, 891.
5. (b) Roush, W. R.; Bennett, C. E. J. Am. Chem. Soc. 1999, 121, 3541.
6. (c) Roush, W. R.; Hartz, R. A.; Gustin, D. J. J. Am. Chem. Soc. 1999, 121, 1990.
7. Yu, B.; Yu, H.; Hui, Y.; Han, X. Synlett 1999, 753.
8. At -78°C, little 1 was consumed. Therefore, the reaction temperature was raised to -10°C; at and above this temperature 3 was produced as the major product.
9. Auzanneau, F.-I.; Bundle, D. R. Carbohydr. Res. 1991, 212, 13.
10. Nicolaou, K. C.; Ladduwahetty, T.; Randall, J. L.; Chucholowski, A. J. Am. Chem. Soc. 1986, 108, 2466.
11. (a) Zuurmond, H. M.; van der Klein, P. A. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1992, 33, 2063.
12. (b) Zuurmond, H. M.; van der Klein, P. A. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1993, 49, 6501.
13. 2, rt, 1.0 h; ~89% for four steps.
14. 2 (0.5 mL). After being stirred for 1 h, the mixture was filtered, concentrated, and applied to a silica gel column (petroleum ether:EtOAc, 8:1) to give 10 (142 mg, 68%) and 15 (28 mg, 25%) as white solids.
15. 3). Compound 16: 4.36 (1H, d, J=8.8 Hz, H-1), 3.18 (1H, dd, J=8.8, 11.3 Hz, H-2).