Efficient synthesis of pyruvic acetals of carbohydrate vicinal diols: 3,4-O-(1-methoxycarbonyl)ethylidene-D-galactopyranoside and 5,6-O-(1-methoxycarbonyl)ethylidene-D-galactofuranoside, via 1-hydroxy-2-propanone acetals

Carbohydrate Research

Volumn 282, Issue 2, 1996, Pages 299-306

  Hiruma, Kazumi ^a,b   Tamura, Jun Ichi ^a,b   Hashimoto, Hironobu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

1 Hydroxy 2 propanone acetals; Pyruvic acetals

Indexed keywords

ACETAL DERIVATIVE; CARBOHYDRATE DERIVATIVE; PYRUVIC ACID DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029959893     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/0008-6215(95)00383-5     Document Type: Article

References (24)

1. B. Lindberg, Adv. Carbohydr. Chem. Biochem., 48 (1990) 279-318.
2. S. Araki, S. Abe, S. Yamada, M. Satake, N. Fujiwara, K. Kon, and S. Ando, J. Biochem., 112 (1992) 461-469.
3. S. Hirase, Bull. Chem. Soc. Jpn., 30 (1957) 70-75.
4. J.H. Sloneker and D.G. Orentas, Nature. 194 (1962) 478-479.
5. H. Niemann, N. Frank, and S. Stirm, Carbohydr. Res., 59 (1977) 165-177.
6. Y.-M. Choy and G.G.S. Dutton, Carbohydr. Res., 52 (1974) 684-687.
7. C. Erbing, L. Kenne, B. Lindberg, J. Lönngren, and I.W. Sutherland, Carbohydr. Res., 50 (1976) 115-120.
8. P.-E. Jannson, B. Lindberg, and U. Lindquist, Carbohydr. Res., 95 (1981) 75-82.
9. M. Beurret, J.-P. Joseleau, M. Vignon, G.G.S. Dutton, and A.V. Savage, Carbohydr. Res., 189 (1989) 247-260.
10. H. Hashimoto, K. Hiruma, and J. Tamura, Carbohydr. Res., 177 (1988) C9-C12.
11. A. Lipták and L. Szabo, Carbohydr. Res., 184 (1988) C5-C8.
12. A. Lipták and L. Szabo, J. Carbohydr. Chem., 8 (1989) 629-644.
13. P.M. Collins, A.C. McKinnon, and A. Manro, Tetrahedron Lett., 30 (1989) 1399-1400.
14. G.O. Aspinall, I.H. Ibrahim, and N.K. Kare, Carbohydr. Res., 200 (1990) 247-256.
15. T. Ziegler, E. Eckhardt, and G. Herold, Liebigs Ann. Chem., (1992) 441-451.
16. K. Hiruma, J. Tamura, S. Horito, J. Yoshimura, and H. Hashimoto, Tetrahedron, 50 (1994) 12143-12158.
17. T. Ziegler and G. Herold, Liebigs Ann. Chem., (1994) 859-866.
18. P.A.J. Gorin and T. Ishikawa, Can. J. Chem., 45 (1967) 521-532.
19. J. Schneider, Y.C. Lee, and H.M. Flowers, Carbohydr. Res., 36 (1974) 159-166.
20. J.F. Stoddart, Stereochemistry of Carbohydrates, Wiley-Interscience, New York, 1971.
21. H. Saeki and T. Iwashige, Chem. Pharm. Bull., 16 (1968) 1129-1132.
22. D.R. Williams, F.D. Klirgler, E.E. Allen, and F.W. Lichtenthaler, Tetrahedron Lett., 29 (1988) 5087-5090.
23. P.J. Garegg and B. Lindberg, Carbohydr. Res., 77 (1979) 71-78.
24. P.A.J. Gorin, M. Mazurek, and H.S. Duarte, Carbohydr. Res., 100 (1982) 101-115.