C2-Acetamidomannosylation. Synthesis of 2-N-acetylamino-2-deoxy-α-D-mannopyranosides with glucal donors

Tetrahedron Letters

Volumn 44, Issue 21, 2003, Pages 4015-4018

  Liu, Jing ^a   Di Bussolo, Valeria ^a,b   Gin, David Y ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

Acetamidomannosylation; Glycosylation; Nitrogen transfer

Indexed keywords

2,8 DIMETHYLDIBENZOTHIOPHENE 5 OXIDE; ACETAMIDE DERIVATIVE; ACID ANHYDRIDE; CARBON; GLUCONATE CALCIUM; OXIDE; PYRANOSIDE; REAGENT; RECEPTOR; TRIFLUOROMETHANESULFONIC ANHYDRIDE; UNCLASSIFIED DRUG;

ACETAMIDOMANNOSYLATION; ADDITION REACTION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DONOR; GLYCOSYLATION;

EID: 0037652302     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00871-2     Document Type: Article

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30. DMDBTO can be easily prepared from commercially available dibenzothiophene in three steps: (1) bromination (Bremner, J. B.; Keller, P. A.; Pyne, S. G.; Robertson, A. D.; Skelton, B. W.; White, A. H.; Witchard, H. M. Aust. J. Chem. 2000, 53, 535-540); (2) methylation (Gilman, H.; Wilder, G. R. J. Org. Chem. 1957, 22, 523-526); and (3) oxidation (Ho, T.-L.; Wong, C. M. Synthesis 1972, 10, 561-562).
31. DMDBTO can be easily prepared from commercially available dibenzothiophene in three steps: (1) bromination (Bremner, J. B.; Keller, P. A.; Pyne, S. G.; Robertson, A. D.; Skelton, B. W.; White, A. H.; Witchard, H. M. Aust. J. Chem. 2000, 53, 535-540); (2) methylation (Gilman, H.; Wilder, G. R. J. Org. Chem. 1957, 22, 523-526); and (3) oxidation (Ho, T.-L.; Wong, C. M. Synthesis 1972, 10, 561-562).
32. The enhancement of yield is likely due to the increased solubility of the sulfonium or sulfurane species formed from DMDBTO.
33. 2 (76 μL, 0.48 mmol, 4.0 equiv.) was added, followed by N-(TMS)acetamide (47 mg, 0.36 mmol, 3.0 equiv.). The mixture was immediately warmed to 23°C and stirred at this temperature for 1 h. A solution of (+)-3-dihydrocholesterol (140 mg, 0.36 mmol, 3.0 equiv.) and CSA (56 mg, 0.24 mmol, 2.0 equiv.) in 1.0 mL dichloromethane was added via cannula and reaction was stirred for 24 h. The mixture was concentrated under vacuum and the residue immediately purified by silica gel flash column chromatography (4:1 hexane/EtOAc, 3:1 PhH/EtOAc) to afford 15 (52 mg, 50% yield) and the corresponding β-gluco diastereomer (10 mg, 10%).
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