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Volumn 50, Issue 36, 2009, Pages 5142-5144

Synthesis of carbadisaccharide mimics of galactofuranosides

Author keywords

Carbasugars; Ethers; Galactofuranose; Pseudodisaccharides

Indexed keywords

ALCOHOL; DISACCHARIDE; EPOXIDE; GALACTOFURANOSIDE DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CARBOHYDRATE SYNTHESIS; CATALYSIS; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY;

EID: 67650480984 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/j.tetlet.2009.06.115 Document Type: Article

Times cited : (4)

References (14)

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- Representative procedure for epoxide-opening; synthesis of 6d: Epoxide 2 (31 mg, 0.072 mmol) and alcohol 3 (150 mg, 0.28 mmol) were dissolved in CH2Cl2 (0.75 mL) under N2 at rt. BF3·OEt2 (18 μL, 0.14 mmol) was dissolved in CH2Cl2 (2.5 mL, and 125 μL (7 μmol) of this solution was added to the reaction mixture, which instantly turned from colourless to pale yellow. After 10 min, TLC (toluene/EtOAc, 5:1) showed complete consumption of epoxide 2 (Rf 0.8, remaining alcohol 3 (Rf 0.4) and the formation of a product (Rf 0.5, The reaction was quenched by addition of Et3N (0.5 mL) and the mixture was concentrated in vacuo. The crude product was purified by column chromatography on silica gel (toluene/EtOAc, 4:1) to give the pseudodisaccharide 6d 48 mg, 69, as a colourless oil
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