Convenient preparation of L-arabino-hexos-5-ulose derivatives from lactose

Carbohydrate Research

Volumn 338, Issue 22, 2003, Pages 2349-2358

  Catelani, Giorgio ^a   Corsaro, Antonino ^b   D'Andrea, Felicia ^a   Mariani, Manuela ^a   Pistarà, Venerando ^b   Vittorino, Elisa ^b  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

Epoxidation; Ketopyranose glycals; L arabino Hexos 5 uloses; Lactose

Indexed keywords

ACETONE; ETHERS; METHANOL; ORGANIC ACIDS; OXIDATION;

EPOXIDATION;

CARBOHYDRATES;

2 O BENZYL 3,4 O ISOPROPYLIDENEARABINOHEXOS 5 ULOSE; 2 O BENZYL 6 O 3 CHLOROBENZOYLARABINOHEXOS 5 ULOSE; 2,6 DI O BENZYLARABINOHEXOS 5 ULOSE; 4 O (2 O BENZYL 6 DEOXY 3,4 O ISOPROPYLIDENE ALPHA ARABINOHEX 5 ENOPYRANOSYL) 2,3:5,6 DI O ISOPROPYLIDENE ALDEHYDRO DEXTRO GLUCOSE DIMETHYL ACETAL; 4 O (2,6 DI O BENZYL 4 DEOXY ALPHA THREO HEX 4 ENOPYRANOSYL) 2,3:5,6 DI O ISOPROPYLIDENE ALDEHYDRO DEXTRO GLUCOSE DIMETHYL ACETAL; ACETAL DERIVATIVE; ACETONE; ARABINOSE DERIVATIVE; DICHLOROMETHANE; LACTOSE; METHANOL; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; EPOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0142200364     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2003.08.001     Document Type: Article

References (22)

1. Part 18 of the series, "Chemical Valorisation of Milk-derived Carbohydrates"; for part 17 see Ref. 22.
2. Theander O. Pigman W., Horton D. The Carbohydrates, Chemistry and Biochemistry. IB:1980;1013-1099 Academic Press.
3. Helferich B., Bigelow N.M. Z. Physiol. Chem. 200:1931;263-276.
4. Kiely D.E., Flechter H.G. Jr. J. Org. Chem. 34:1969;1386-1390.
5. Ferrier R.J., Tyler P.C. J. Chem. Soc., Perkin 1. 1980;1528-1534.
6. Heusinger H. Carbohydr. Res. 181:1988;67-76.
7. Baxter E.W., Reitz A.B. J. Org. Chem. 59:1994;3175-3185.
8. Barili P.L., Berti G., Catelani G., D'Andrea F., De Rensis F., Puccioni L. Tetrahedron. 53:1997;3407-3416.
9. Pistarà V., Barili P.L., Catelani G., Corsaro A., D'Andrea F., Fisichella S. Tetrahedron Lett. 41:2000;3253-3256.
10. Catelani G., Corsaro A., D'Andrea F., Mariani M., Pistarà V. Biorg. Med. Chem. Lett. 12:2002;3313-3315.
11. Barili P.L., Berti G., Catelani G., D'Andrea F. Gazz. Chim. Ital. 122:1992;135-142.
12. Barili P.L., Berti G., Catelani G., D'Andrea F., De Rensis F. Tetrahedron. 53:1997;8665-8674.
13. Enright P.M., Tosin M., Nieuwenhuyzen M., Ceroni L., Murphy P.V. J. Org. Chem. 67:2002;3733-3741.
14. Corsaro, A.; Catelani, G.; D'Andrea, F.; Fisichella, S.; Mariani, M.; Pistarà, V. "4° Convegno Consorzio Interuniversitario Nazionale La Chimica per l'Ambiente (INCA)" Santa Margherita Ligure (Italy) 25-28 February 2001. Proceedings in Environ. Sci. Pollut. Res. OnlineFirst [DOI: http://dx.doi.org/10.1065/espr2001.12.104.2].
15. Barili P.L., Catelani G., D'Andrea F., De Rensis F., Falcini P. Carbohydr. Res. 298:1997;75-84.
16. Stevens J.D. Carbohydr. Res. 45:1975;143-150.
17. Capozzi G., Catelani G., D'Andrea F., Menichetti S., Nativi C. Carbohydr. Res. 338:2003;123-132.
18. Barili P.L., Berti G., Catelani G., D'Andrea F., Puccioni L. J. Carbohydr. Chem. 19:2000;79-91.
19. Tsuzuki K., Nakajima Y., Watanabe T., Yanagiya M., Matsumoto T. Tetrahedron Lett. 11:1978;989-992.
20. Bock K., Pedersen C. Adv. Carbohydr. Chem. Biochem. 41:1983;27-66.
21. Perrin D.D., Armarego W.L.F., Perrin D.R. Purification of Laboratory Chemicals. 2nd ed:1980;Pergamon Press, Oxford.
22. Attolino E., Catelani G., D'Andrea F. Tetrahedron Lett. 43:2002;8815-8818.