Synthesis of β-d-arabinofuranosides: stereochemical differentiation between d- and l-enantiomers

Carbohydrate Research

Volumn 343, Issue 18, 2008, Pages 3100-3106

  Wang, Yingxi ^a   Maguire Boyle, Samuel ^a   Dere, Ravindra T ^a   Zhu, Xiangming ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

d Arabinofuranoside; Glycosylation; Protecting groups; Thioglycoside

Indexed keywords

DIFFERENTIATION (CALCULUS); GLYCOSYLATION;

AS PROMOTERS; GLYCOSYL ACCEPTORS; HIGH YIELDS; PROTECTING GROUPS; STEREOCHEMICAL DIFFERENTIATIONS; STEREOSELECTIVE MANNERS; SYNTHESIS OF; THIOGLYCOSIDE;

ESTERIFICATION;

2 O BENZYL 3,5 O (DI TERT BUTYLSILANEDIYL) ALPHA BETA DEXTRO ARABINOFURANOSYL (1-6) 1,2;3,4 DI O ISOPROPYLIDENE ALPHA DEXTRO GALACTOPYRANOSE; 2 O BENZYL 3,5 O (DI TERT BUTYLSILANEDIYL) ALPHA DEXTRO ARABINOFURANOSYL TRICHLOROACETIMIDATE; 3,5 O (DI TERT BUTYLSILANEDIYL) 2 O (2 TRIFLUOROMETHYLBENZENESULFONYL) ALPHA BETA DEXTRO ARABINOFURANOSYL (1-6) 1,2;3,4 DI O ISOPROPYLIDENE ALPHA DEXTRO GALACTOPYRANOSE; ARABINOSIDE; CARBOHYDRATE DERIVATIVE; DISACCHARIDE; METHYL 2 O BENZYL 3,5 O (DI TERT BUTYLSILANEDIYL) ALPHA BETA DEXTRO ARABINOFURANOSYL (1-3) 2 O BENZOYL 4,6 O BENZYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2 O BENZYL 3,5 O (DI TERT BUTYLSILANEDIYL) ALPHA BETA DEXTRO ARABINOFURANOSYL (1-4) 2,3,6 TRI O ACETYL BETA DEXTRO GALACTOPYRANOSIDE; METHYL 2 O BENZYL 3,5 O (DI TERT BUTYLSILANEDIYL) ALPHA BETA DEXTRO ARABINOFURANOSYL (1-6) 2,3,4 TRI O ACETYL BETA DEXTRO GALACTOPYRANOSIDE; METHYL 2 O BENZYL 3,5 O (DI TERT BUTYLSILANEDIYL) ALPHA BETA DEXTRO ARABINOFURANOSYL (1-6) 2,3,4 TRI O BENZOYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2 O BENZYL 3,5 O (DI TERT BUTYLSILANEDIYL) ALPHA BETA DEXTRO ARABINOFURANOSYL (1-6) 2,3,4 TRI O BENZOYL ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 2 O BENZYL 3,5 O (DI TERT BUTYLSILANEDIYL) ALPHA BETA DEXTRO ARABINOFURANOSYL (1-6) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; PHENYL 2 O BENZYL 3,5 O (DI TERT BUTYLSILANEDIYL) 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; PHENYL 2,3,5 TRI O ACETYL 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; PHENYL 3,5 O (DI TERT BUTYLSILANEDIYL) 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; PHENYL 3,5 O (DI TERT BUTYLSILANEDIYL) 2 O (2 TRIFLUOROMETHYLBENZENESULFONYL) 1 THIO ALPHA DEXTRO ARABINOFURANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; ENANTIOMER; GLYCOSYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ARABINOSE; CARBOHYDRATE SEQUENCE; GLYCOSYLATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 55049104772     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2008.09.006     Document Type: Article

References (34)

1. Fincher G.B., and Stone B.A. Ann. Rev. Plant Physiol. 34 (1983) 47-70
2. Ridley B.L., O'Neill M.A., and Mohnen D. Phytochemistry 57 (2001) 929-967
3. Lowary T.L. Curr. Opin. Chem. Biol. 7 (2003) 749-756
4. For examples, see:. Mereyala H.B., Hotha S., and Gurjar M.K. Chem. Commun. (1998) 685-686
5. D'Souza F.W., and Lowary T.L. Org. Lett. 2 (2000) 1493-1495
6. Sanchez S., Bamhaoud T., and Prandi J. Tetrahedron Lett. 41 (2000) 7447-7452
7. Bamhaoud T., Sanchez S., and Prandi J. Chem. Commun. (2000) 659-660
8. Yin H., D'Souza F.W., and Lowary T.L. J. Org. Chem. 67 (2002) 892-903
9. Lowary T.L. J. Carbohydr. Chem. 21 (2002) 691-722
10. Marotte K., Sanchez S., Bamhaoud T., and Prandi J. Eur. J. Org. Chem. (2003) 3587-3598
11. Rao Y., and Boons G.J. Angew. Chem., Int. Ed. 46 (2007) 6148-6151
12. For examples, see:. Gadikota R.R., Callam C.S., and Lowary T.L. Org. Lett. 3 (2001) 607-610
13. Callam C.S., Gadikota R.R., Krein D.M., and Lowary T.L. J. Am. Chem. Soc. 125 (2003) 13112-13119
14. Gadikota R.R., Callam C.S., Wagner T., Fraino B.D., and Lowary T.L. J. Am. Chem. Soc. 125 (2003) 4155-4165
15. Désiré J., and Prandi J. Carbohydr. Res. 317 (1999) 110-118
16. Lee Y.J., Lee K., Jung E.H., Jeon H.B., and Kim K.S. Org. Lett. 7 (2005) 3263-3266
17. Zhu X., Kawatkar S., Rao Y., and Boons G.J. J. Am. Chem. Soc. 128 (2006) 11948-11957
18. Ishiwata A., Akao H., and Ito Y. Org. Lett. 8 (2006) 5525-5528
19. Crich D., Pedersen C.M., Bowers A.A., and Wink D.J. J. Org. Chem. 72 (2007) 1553-1565
20. NIS/AgOTf has been used to activate conformationally unconstrained thioarabinofuranosides, see:. Yin H., and Lowary T.L. Tetrahedron Lett. 42 (2001) 5829-5832
21. Kam B.L., Barascut J.L., and Imbach J.L. Carbohydr. Res. 69 (1979) 135-142
22. Nacario R.C., Lowary T.L., and McDonald R. Acta Crystallogr., Sect. E 63 (2007) o498-o500
23. Agnihotri G., and Misra A.K. Carbohydr. Res. 341 (2006) 2420-2425
24. Spijker N.M., and van Boeckel C.A.A. Angew. Chem., Int. Ed. Engl. 30 (1991) 180-183
25. Jiao H., and Hindsgaul O. Angew. Chem., Int. Ed. 38 (1999) 346-348
26. Yan M.C., Chen Y.N., Wu H.T., Lin C.C., Chen C.T., and Lin C.C. J. Org. Chem. 72 (2007) 299-302
27. Kumar G.D.K., and Baskaran S. J. Org. Chem. 70 (2005) 4520-4523
28. Manthorpe J.M., Szpilman A.M., and Carreira E.M. Synthesis (2005) 3380-3388
29. Kiefel M.J., Beisner B., Bennett S., Holmes I.D., and von Itzstein M. J. Med. Chem. 39 (1996) 1314-1320
30. Joe M., Bai Y., Nacario R.C., and Lowary T.L. J. Am. Chem. Soc. 129 (2007) 9885-9901
31. Rademacher C., Shoemaker G.K., Kim H.S., Zheng R.B., Taha H., Liu C., Nacario R.C., Schriemer D.C., Klassen J.S., Peters T., and Lowary T.L. J. Am. Chem. Soc. 129 (2007) 10489-10502
32. Schmidt R.R., and Kinzy W. Adv. Carbohydr. Chem. Biochem. 50 (1994) 21-123
33. Crich D., Hutton T.K., Banerjee A., Jayalath P., and Picione J. Tetrahedron: Asymmetry 16 (2005) 105-119
34. Abdel-Rahman A.A.H., Jonke S., El Ashry E.S.H., and Schmidt R.R. Angew. Chem., Int. Ed. 41 (2002) 2972-2974