Unusual addition of amines to C-2 of vinyl sulfone-modified-β-d-pent-2-enofuranosyl carbohydrates: synthesis of a new class of β-anomeric 2-amino-2,3-dideoxy-d-threo-pentofuranosides

Carbohydrate Research

Volumn 343, Issue 8, 2008, Pages 1287-1296

  Das, Indrajit ^a,b   Suresh, Cheravakkattu G ^c   Décout, Jean Luc ^b   Pathak, Tanmaya ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b Laboratoire de Pharmacochimie   (France)

^c NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Amino sugars; Deoxyaminosugars; Desulfonylation with Mg MeOH NiBr2; Diastereoselective Michael addition; Vinyl sulfone modified carbohydrates

Indexed keywords

ADDITION REACTIONS; AMINES; NUCLEOPHILES; SYNTHESIS (CHEMICAL);

AMINO SUGARS; DEOXYAMINOSUGARS; DESULFONYLATION; DIASTEREOSELECTIVE MICHAEL ADDITION; DIASTEREOSELECTIVITY; VINYL SULFONE-MODIFIED CARBOHYDRATES;

CARBOHYDRATES;

AMINE; AMINOSUGAR; METHYL 2 ACETYLAMINO 5 O BENZYL 2,3 DIDEOXY BETA DEXTRO THREOPENTOFURANOSIDE; METHYL 2 AMINO 5 O BENZYL 2,3 DIDEOXY(3 C 4 TOLYLSULFONYL)ALPHA DEXTRO ARABINOFURANOSIDE; METHYL 2 AMINO 5 O BENZYL 2,3 DIDEOXY(3 C 4 TOLYLSULFONYL)BETA DEXTRO ARABINOFURANOSIDE; METHYL 2 AMINO 5,6 O CYCLOHEXYLIDENE 2,3 DIDEOXY 2 PYRROLIDINO(3 C 4 TOLYLSULFONYL)BETA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 ANHYDRO 5,6 O CYCLOHEXYLIDENE ALPHA DEXTRO MANNOFURANOSIDE; METHYL 5 O BENZYL 2 ACETYLAMINO 2,3 DIDEOXY BETA DEXTRO THREOPENTOFURANOSIDE; METHYL 5 O BENZYL 2 CYCLOHEXAMINO 2,3 DIDEOXY BETA DEXTRO THREOPENTOFURANOSIDE; METHYL 5 O BENZYL 2 CYCLOHEXYLAMINO 2,3 DIDEOXY(3 C 4 TOLYLSULFONYL)BETA DEXTRO ARABINOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 MORPHOLINO BETA DEXTRO ERYTHROPENTOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 MORPHOLINO BETA DEXTRO THREOPENTOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 MORPHOLINO(3 C 4 TOLYLSULFONYL)BETA DEXTRO ARABINOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 MORPHOLINO(3 C 4 TOLYLSULFONYL)BETA DEXTRO XYLOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 PYRRLIDINO(3 C 4 TOLYLSULFONYL)ALPHA DEXTRO ARABINOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 PYRROLIDINO(3 C 4 TOLYLSULFONYL)BETA DEXTRO ARABINOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY(3 C 4 TOLYLSULFONYL)BETA DEXTRO ARABINOFURANOSIDE; METHYL 5,6 O CYCLOHEXYLIDENE 2,3 DIDEOXY 2 PYRROLIDINO(3 C 4 TOLYLSULFONYL)ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 5,6 O CYCLOHEXYLIDENE 2,3 DIDEOXY 2 PYRROLIDINO(3 C 4 TOLYLSULFONYL)BETA DEXTRO GLUCOPYRANOSIDE; METHYL 5,6 O CYCLOHEXYLIDENE 2,3 DIDEOXY 2 PYRROLIDINO(3 C 4 TOLYLSULFONYL)BETA DEXTRO MANNOPYRANOSIDE; METHYL 5,6 O CYCLOHEXYLIDENE 2,3 DIDEOXY(3 C 4 TOLYLSULFONYL)ALPHA DEXTRO ERYTHRO HEX 2 ENOPYRANOSIDE; METHYL 5,6 O CYCLOHEXYLIDENE 2,3 DIDEOXY(3 C 4 TOLYLSULFONYL)ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 5,6 O CYCLOHEXYLIDENE 2,3 DIDEOXY(3 C 4 TOLYLSULFONYL)BETA DEXTRO ERYTHRO HEX 2 ENOPYRANOSIDE; METHYL 5,6 O CYCLOHEXYLIDENE 3 DEOXY(3 C 4 TOLYLSULFONYL)ALPHA DEXTRO ALLOPYRANOSIDE; METHYL 5,6 O CYCLOHEXYLIDENE 3 DEOXY(3 C 4 TOLYLSULFONYL)ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 5,6 O CYCLOHEXYLIDENE 3 DEOXY(3 C 4 TOLYLSULFONYL)BETA DEXTRO ALLOPYRANOSIDE; NITROGEN; SULFONE DERIVATIVE; VINYL DERIVATIVE;

ADDITION LINE; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

AMINES; AMINO SUGARS; AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; DEOXY SUGARS; FURANS; STEREOISOMERISM; SULFONES;

EID: 43049107144     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2008.03.022     Document Type: Article

References (27)

1. McAuliffe J.C., and Hindsgaul O. Chem. Ind. (London) (1997) 170-175
2. Kondo S., and Hotta K. J. Infect. Chemother. 5 (1999) 1-9
3. Wong C.-H. Acc. Chem. Res. 32 (1999) 376-385
4. Ravindran B., and Pathak T. J. Org. Chem. 64 (1999) 9715-9718
5. Ravindran B., Sakthivel K., Suresh C.G., and Pathak T. J. Org. Chem. 65 (2000) 2637-2641
6. Ravindran B., and Pathak T. Ind. J. Chem. B40 (2001) 1114-1120
7. Ravindran B., Deshpande S.G., and Pathak T. Tetrahedron 57 (2001) 1093-1098
8. Suresh C.G., Ravindran B., Pathak T., Narasimha Rao K., Sasidhar Prasad J.S., and Lokanath N.K. Carbohydr. Res. 337 (2002) 1507-1512
9. Sanki A.K., and Pathak T. Synlett (2002) 1241-1244
10. Sanki A.K., and Pathak T. Tetrahedron 59 (2003) 7203-7214
11. Hanessian S., and Masse R. Carbohydr. Res. 35 (1974) 175-185
12. Sanki A.K., Suresh C.G., Falgune U.D., and Pathak T. Org. Lett. 5 (2003) 1285-1288
13. Das I., and Pathak T. Org. Lett. 8 (2006) 1303-1306
14. Casini G., and Goodman L. J. Am. Chem. Soc. 86 (1964) 1427-1431
15. Montgomery J.N., Thorpe M.C., Clayton S.D., and Thomas H.J. Carbohydr. Res. 32 (1974) 404-407
16. Bock K., and Pederson C. Carbohydr. Res. 73 (1979) 85-91
17. Liptak A., Neszmelyi A., Kovac P., and Hirsch J. Tetrahedron 37 (1981) 2379-2382
18. Su T.-L., Klein R.S., and Fox J.J. J. Org. Chem. 46 (1981) 1790-1792
19. Kawana M., Kuzuhara H., and Emoto S. Bull. Chem. Soc. Jpn. 54 (1981) 1492-1504
20. Kawana M., Koresawa T., and Kuzuhara H. Bull. Chem. Soc. Jpn. 56 (1983) 1095-1100
21. Najera C., and Yus M. Tetrahedron 55 (1999) 10547-10658
22. Chan M.C., Cheng K.M., Ho K.M., Ng C.T., Yam T.M., Wang B.S.L., and Luh T.Y. J. Org. Chem. 53 (1988) 4466-4471
23. Oikawa M., Oikawa H., and Ichthara A. Tetrahedron Lett. 34 (1993) 4797-4800
24. Oikawa M., Oikawa H., and lchihara A. Tetrahedron 51 (1995) 6237-6254
25. Gamble M.P., Giblin G.M.P., and Taylor R.J.K. Synlett (1995) 779-780
26. Mauret P., and Alphonse P. J. Org. Chem. 47 (1982) 3322-3323
27. Kawana, M.; Kuzuhara, H. Synthesis 1995, 544-552.