Fragmentation of carbohydrate anomeric alkoxyl radicals: Synthesis of chiral 1-bromo-1-fluoro-1-iodo-alditols

Tetrahedron Asymmetry

Volumn 15, Issue 1, 2004, Pages 11-14

  Francisco, Cosme G ^a   González, Concepción C ^a   Kennedy, Alan R ^b   Paz, Nieves R ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

(DIACETOXYIODO)BENZENE; 2 BROMO 2 DEOXY 2 FLUOROHEXOPYRANOSE; 2 BROMO 2 DEOXY 2 FLUOROPENTOPYRANOSE; ALDITOL; BENZENE DERIVATIVE; BROMINE DERIVATIVE; CARBOHYDRATE DERIVATIVE; CARBON; FLUORINE DERIVATIVE; IODINE; IODINE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CHROMATOGRAPHY; FRAGMENTATION REACTION; LIGHT IRRADIANCE; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0346787774     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.016     Document Type: Article

References (28)

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23. 2O (1 mL), containing recently crystallized N-bromoacetamide (1.5 mmol) was stirred at room temperature for 1-4 h. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic layer was dried and concentrated in vacuo. Column chromatography of the residue (hexanes-EtOAc mixtures) afforded the required bromohydrin compounds.
24. 2. The organic layer was washed with 10% aqueous sodium thiosulfate, dried and concentrated in vacuo. Chromatotron chromatography of the residue (hexanes-EtOAc mixtures) afforded the required halo-iodine compounds.
25. 10: C, 30.94; H, 2.43; N, 4.51. Found: C, 31.06; H, 2.41; N, 4.48.
26. o|>2σ(
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