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Volumn 19, Issue 17, 2008, Pages 1999-2002

Novel Galf-disaccharide mimics: synthesis by way of 1,3-dipolar cycloaddition reactions in water

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIDEOXY 1,4 IMINOGALACTITOL; ALLYL COMPOUND; ARABINOSE; DISACCHARIDE; ENZYME INHIBITOR; FURAN; GALACTITOL; GALACTOFURANOSE DISACCHARIDE; GALACTOFURANOSE TRANSFERASE; GALACTOSE; GLYCAN DERIVATIVE; NITRONE DERIVATIVE; TRANSFERASE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; WATER;

EID: 51449096417     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.08.006     Document Type: Article
Times cited : (25)

References (52)
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    • note
    • By allylation (AllBr, NaH, DMF) of methyl 2,3-di-O-benzyl-l-arabinofuranoside, obtained according to Ref. 15.
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    • note
    • All new compounds gave correct elemental analyses and/or HRMS data.
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    • Experimental procedure for 5: To a solution of methyl 2,3-di-O-benzyl-β-l-arabino-pentodialdofuranoside:
    • Experimental procedure for 5: To a solution of methyl 2,3-di-O-benzyl-β-l-arabino-pentodialdofuranoside:. Tadahiro I., and Hiromichi S. Chem. Pharm. Bull. 15 (1967) 132-135
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    • (170 mg, 0.50 mmol) in THF (3.4 mL) was added, at 0 °C, a 1 M solution of vinylmagnesium bromide in THF (2 mL). After stirring for 3 h at 0 °C and 12-14 h at rt, the reaction was quenched by adding saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The organic phase was separated, washed with brine and dried over sodium sulfate. Solvents were evaporated, and purification on silica gel afforded compound 5 (130 mg, 71%) as a mixture of separable diastereoisomers (dr 28:72)
    • Hiromichi S., and Tadahiro I. Chem. Pharm. Bull. 16 (1968) 1129-1132 (170 mg, 0.50 mmol) in THF (3.4 mL) was added, at 0 °C, a 1 M solution of vinylmagnesium bromide in THF (2 mL). After stirring for 3 h at 0 °C and 12-14 h at rt, the reaction was quenched by adding saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The organic phase was separated, washed with brine and dried over sodium sulfate. Solvents were evaporated, and purification on silica gel afforded compound 5 (130 mg, 71%) as a mixture of separable diastereoisomers (dr 28:72)
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  • 32
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    • For a review on imino-C-disaccharides synthesis:
    • For a review on imino-C-disaccharides synthesis:. Robina I., and Vogel P. Synthesis (2005) 675-702
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  • 34
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    • For related imino-C-disaccharides precursors see:
    • For related imino-C-disaccharides precursors see:. Cardona F., Goti A., and Brandi A. Org. Lett. 5 (2003) 1475-1478
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    • note
    • Synthesis of compound 9: Methyl β-d-galactofuranoside (494 mg, 2.55 mmol) was dissolved in MeOH (30 mL). Dibutyltin oxide (1.27 g, 5.09 mmol) was then added and the reaction mixture was stirred for 4 h at 70 °C. After concentration under reduced pressure, the white foamy material was dissolved in THF (3.5 mL). After the addition of tetrabutylammonium iodide (940 mg, 2.54 mmol) and allyl bromide (488 μL, 5.61 mmol), the mixture was stirred overnight at rt and then for 48 h at 50 °C. After concentration under reduced pressure, purification on silica gel (EP/AcOEt 4/1 and then 2/1) afforded the desired compound 9 (382 mg, 64%) as a yellowish oil.
  • 42
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    • Desvergnes, V.; Biltresse, S.; Martin, O.R. Conception et Synthèse d'Analogues du Galactofuranose. Presented at the National Organic Symposium of the French Chemical Society (JCO), Palaiseau, France, September 7-9, 2004; Abstract P268.
    • Desvergnes, V.; Biltresse, S.; Martin, O.R. Conception et Synthèse d'Analogues du Galactofuranose. Presented at the National Organic Symposium of the French Chemical Society (JCO), Palaiseau, France, September 7-9, 2004; Abstract P268.
  • 44
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    • note
    • 2O 7/4/0.1) afforded the desired cycloadduct.
  • 51
    • 20444497757 scopus 로고    scopus 로고
    • See also: and reference cited therein
    • See also:. Muzart J. Tetrahedron 61 (2005) 5955-6008 and reference cited therein
    • (2005) Tetrahedron , vol.61 , pp. 5955-6008
    • Muzart, J.1


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