Synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans via chemoselective hydrogenation of hex-2-enopyranosyl acetates

Tetrahedron Letters

Volumn 47, Issue 47, 2006, Pages 8271-8274

  Sasaki, Kaname ^a   Wakamatsu, Takayuki ^a   Matsumura, Shuichi ^a   Toshima, Kazunobu ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Carbohydrates; Chemoselectivity; Hydrogenation; Hydrogenolysis; Tetrahydropyrans

Indexed keywords

ACETIC ACID DERIVATIVE; ALUMINUM OXIDE; RHODIUM; SOLVENT; TETRAHYDROPYRAN DERIVATIVE; TOLUENE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYSIS; HYDROGENATION; LOW TEMPERATURE; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; TEMPERATURE DEPENDENCE;

EID: 33750018084     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.091     Document Type: Article

References (12)

1. For a perspective article, see:. Toshima K. Carbohydr. Res. 341 (2006) 1282-1297
2. For recent reviews of synthesis of natural products using carbohydrates as chiral starting materials, see:. Chapleur Y., and Chrétien F. In: Levy D.E., and Fügedi P. (Eds). The Organic Chemistry of Sugars (2006), CRC Press, Boca Raton 489-573
3. Tatsuta K., and Hosokawa S. Chem. Rev. 105 (2005) 4707-4729
4. Nicolaou K.C., and Mitchell H.J. Angew. Chem., Int. Ed. 40 (2001) 1576-1624
5. Hudlický M. Reductions in Organic Chemistry (1984), John Wiley & Sons, New York
6. Omura S., Tanaka H., Oiwa R., Awaya J., Masuma R., and Tanaka K. J. Antibiot. 30 (1977) 908-916
7. Imamura N., Kakinuma N., Ikekawa H., Tanaka H., and Omura S. J. Antibiot. 34 (1981) 1517-1518
8. For synthesis of 1 by a single step from tri-O-acetyl-d-glucal, see:. Inaba K., Matsumura S., and Yoshikawa S. Chem. Lett. 20 (1991) 485-488
9. By an easy and efficient two steps, see:. Baer H.H., and Siemsen L. Carbohydr. Res. 134 (1984) 49-61
10. Nicolaou K.C., Hwang C.-K., Marron B.E., DeFrees S.A., Couladouros E.A., Abe Y., Carroll P.J., and Snyder J.P. J. Am. Chem. Soc. 112 (1990) 3040-3054
11. 2/C in hydrogenolysis, see:. Toshima K., Yanagawa K., Mukaiyama S., and Tatsuta K. Tetrahedron Lett. 31 (1990) 6697-6698
12. Tsuji J., and Yamakawa T. Tetrahedron Lett. 20 (1979) 613-616