Regioselective ring opening of benzylidene acetal protecting group(s) of hexopyranoside derivatives by DIBAL-H

Carbohydrate Research

Volumn 343, Issue 15, 2008, Pages 2675-2679

  Tanaka, Nobuo ^a   Ogawa, Izumi ^a   Yoshigase, Shigeki ^a   Nokami, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Benzylidene acetal; Deprotection; DIBAL H; Reduction; Solvent effect

Indexed keywords

AROMATIC HYDROCARBONS; CARBOHYDRATES; COMPUTER NETWORKS; DICHLOROMETHANE; FULLERENES; ORGANIC SOLVENTS; SOLVENTS; TOLUENE;

BENZYLIDENE ACETAL; DEPROTECTION; DIBAL-H; REDUCTION; SOLVENT EFFECT;

SOLUTIONS;

2,3-DI O BENZYL 4,6 O BENZYLIDENE ALPHA DEXTRO GALACTOSIDE; BENZYLIDENE DERIVATIVE; CARBOHYDRATE DERIVATIVE; DICHLOROMETHANE; DIISOBUTYLALUMINIUM HYDRIDE; GLUCOSIDE; MANNOSIDE; METHYL 2 O BENZYL 4,6 O BENZYLIDENE ALPHA DEXTRO MANNOSIDE; METHYL 2,3 4,6 DI O BENZYLIDENE ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 2,3 DI O BENZYL 4,6 O BENZYLIDENE ALPHA DEXTRO GLUCOSIDE; METHYL 2,3 DI O BENZYL 4,6 O BENZYLIDENE ALPHA DEXTRO MANNOSIDE; METHYL 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3,4 TRI O BENZYL ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 2,3,6 TRI O BENZYL ALPHA DEXTRO GALACTOSIDE; METHYL 2,3,6 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3,6 TRI O BENZYL ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 3 O BENZYL 4,6 O BENZYLIDENE ALPHA DEXTRO MANNOSIDE; PYRANOSIDE; REDUCING AGENT; SOLVENT; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; DEPROTECTION REACTION; DERIVATIZATION; ISOMER; PRIORITY JOURNAL; REDUCTION; RING OPENING; STEREOCHEMISTRY;

ACETALS; CARBOHYDRATE CONFORMATION; CHEMISTRY; DISACCHARIDES; DRUG DESIGN; GALACTOSIDES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PYRANS; SOLVENTS; STEREOISOMERISM; TIME FACTORS;

EID: 51249117103     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2008.07.017     Document Type: Article

References (22)

1. Hanessian S. Total Synthesis of Natural Products: The 'Chiron' Approach (1983), Pergamon Press, Oxford
2. Wnag C.-C., Lee J.-C., Luo S.-Y., Kulkarni S.S., Huang Y.-W., Lee C.-C., Chang K.-L., and Hung S.-C. Nature 446 (2007) 896-899
3. Reductive deprotection of 4,6-O-benzylidene acetal of 1 to give the corresponding 4-O-benzyl derivative 2; using DIBAL-H:. Mikami T., Asano H., and Mitsunobu O. Chem. Lett (1987) 2033-2036
4. 3:. Lipták A., Jodál I., and Nánási P. Carbohydr. Res. 44 (1975) 1-11
5. 2BOTf:. Jiang L., and Chan T.-H. Tetrahedron Lett. 39 (1998) 355-358
6. 2:. Wang C.-C., Luo S.-Y., Shie C.-R., and Hung S.-C. Org. Lett. 4 (2002) 847-849
7. 2:. Shie C.-R., Tzeng Z.-H., Kulkarni S.S., Uang B.-J., Hsu C.-Y., and Hung S.-C. Angew. Chem., Int. Ed. 44 (2005) 1665-1668
8. 2:. Tani S., Sawadi S., Kojima M., Akai S., and Sato K. Tetrahedron Lett. 48 (2007) 3103-3104
9. 2:. Oikawa M., Liu W.-C., Nakai Y., Koshida S., Fukase K., and Kusumoto S. Synlett (1996) 1179-1180
10. 3 in THF:. Ek M., Garegg J., Hultberg H., and Oscarson S. J. Carbohydr. Chem. 2 (1983) 305-311
11. 3-HCl:. Garegg P.J., and Hultberg H. Carbohydr. Res. 93 (1981) C10-C11
12. Garegg P.J., Hultberg H., and Wallin S. Carbohydr. Res. 108 (1982) 97-101
13. 2H:. DeNinno M.P., Etienne J.B., and Duplantier K.C. Tetrahedron Lett. 36 (1995) 669-672
14. 2O:. Debenham S.D., and Toone E.J. Tetrahedron: Asymmetry 11 (2000) 385-387
15. Suzuki K., Nonaka H., and Yamaura M. J. Carbohydr. Chem. 23 (2004) 253-259
16. Ennis S.C., Cumpstey I., Fairbanks A.J., Butters T.D., Mackeen M., and Wormald M.R. Tetrahedron 58 (2002) 9403-9411
17. Lipták A., Czégény L., Harangi J., and Nánási P. Carbohydr. Res. 73 (1979) 327-331
18. Bhattacharjee S.S., and Gorin P.A.J. Can. J. Chem. 47 (1969) 1195-1206
19. Bhattacharjee S.S., and Gorin P.A.J. Can. J. Chem. 47 (1969) 1207-1215
20. Patroni J.J., Stick R.V., Skelton B.W., and White A.H. Aust. J. Chem. 41 (1988) 91-102
21. Ferro V., Mocerino M., Stick R.V., and Tilbrook D.M.G. Aust. J. Chem. 41 (1988) 813-815
22. Lipták A., Czegeny I., Janos H., and Nánási P. Carbohydr. Res. 73 (1970) 327-331