Microwave-induced, Montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-D-galactal: Mild, eco-friendly, rapid glycosidation with allylic rearrangement

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6795-6798

  Shanmugasundaram, Bhagavathy ^a,b   Bose, Ajay K ^b   Balasubramanian, Kalpattu K ^a,c  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

^b STEVENS INSTITUTE OF TECHNOLOGY   (United States)

^c Shasun Chemicals and Drugs Ltd   (India)

Author keywords

Ferrier rearrangement; Galactal; Glucal; Microwave irradiation; Montmorillonite K10

Indexed keywords

2 DEOXY DEXTRO LYXOHEXOPYRANOSIDE; 2,3 DIDEOXY DEXTRO THREO HEX 2 ENOPYRANOSIDE; 3,4,6 TRI O ACETYL DEXTRO GLUCAL; ALKYL GROUP; CHEMICAL COMPOUND; GLUCONATE CALCIUM; MONTMORILLONITE; PYRANOSIDE; TRI O ACETYL DEXTRO GALACTAL; UNCLASSIFIED DRUG;

ALLELE; ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; GLYCOSIDATION; MICROWAVE RADIATION;

EID: 0037119676     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01517-4     Document Type: Article

References (20)

1. Williams N.R., Wander J.D. The Carbohydrates. Chemistry and Biochemistry. 1980;761-798 Academic Press, New York.
2. Ferrier R.J., Prasad N. J. Chem. Soc. C. 1969;570-574.
3. . For a recent review on the Ferrier rearrangement, see: Ferrier R.J. Topics Curr. Chem. 215:2001;153-175.
4. . For review on glycosidation, see: Toshima K., Tatsuta K. Chem. Rev. 93:1993;1503-1531.
5. Ramesh N.G., Balasubramanian K.K. Tetrahedron Lett. 33:1992;3061-3064.
6. Sabesan S., Neira S. J. Org. Chem. 56:1991;5468-5472.
7. Sobhana Babu B., Balasubramanian K.K. Carbohydr. Lett. 3:1999;339-342.
8. Descotes G., Martin J.C. Carbohydr. Res. 56:1977;168-172.
9. Sobhana Babu B., Balasubramanian K.K. Tetrahedron Lett. 41:2000;1271-1274.
10. Pearson W.H., Schkeryantz M. J. Org. Chem. 57:1992;2986-2987.
11. Yadav J.S., Reddy S., Murthy C.V.S.R., Kumar M.G. Synlett. 10:2000;1450-1451.
12. Koreeda M., Houston T.A., Shull B.K., Klemke E., Tuinman R. Synlett. 1995;90-92.
13. Toshima K., Ishizuka T., Matsuo G., Nakata M., Kinoshito M. J. Chem. Soc., Chem. Commun. 1993;704-706.
14. Sobhana Babu B., Balasubramanian K.K. Synth. Commun. 29:1999;4299-4305.
15. Grynkiewicz G., Priebe W., Zamojski A. Carbohydr. Res. 68:1979;33-41.
16. Lakshmi R. Ph.D. Thesis, Indian Institute of Technology Madras, Chennai, India, 2002.
17. Toshima K., Ishizuka G., Matsuo G., Nakata M. Synlett. 1995;306-308.
18. Sowmya S., Balasubramanian K.K. Synth. Commun. 24:1994;2097-2101.
19. Bose A.K., Banik B.K., Lavlinskaia N., Jayaraman M., Manhas M.S. Chem. Tech. 27:1997;18-24.
20. Juarasti E., Cuevas G. The Anomeric Effect. 1995;CRC, Boca Raton.