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Volumn 42, Issue 18, 2003, Pages 2047-2051

Oligosaccharide synthesis on a fluorous support

Author keywords

Fluorine; Glycosylation; Oligosaccharides; Synthetic methods

Indexed keywords

CATALYST SUPPORTS; CHEMICAL BONDS; ORGANIC SOLVENTS; SOLVENT EXTRACTION; SPECTROSCOPY; SYNTHESIS (CHEMICAL);

EID: 0038249096     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250531     Document Type: Article
Times cited : (100)

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    • note
    • Product mixtures containing the fluorous compounds 10, 13, and 20 were partitioned between FC-72 and MeOH. Those containing the fluorous compounds 11 and 18 were partitioned between FC-72, toluene, and water. The product mixture containing the fluorous compound 17 was partitioned between FC-72 and acetonitrile. None of the fluorous compounds were detected by TLC of the organic layer after three extractions with FC-72, which shows that these compounds were quantitatively extracted with FC-72.
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    • The anomer ratio of compound 13 (at the newly formed anomeric position) was determined to be α/β = 50:50 by NMR spectroscopic analysis.
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    • 9 is a commercially available fluorocarbon solvent (3 M, Tokyo) called Novec HFE-7200.
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    • note
    • FC-72 is a commercially available fluorocarbon solvent (3 M, Tokyo) called Fluorinert FC-72, which consists of perfluorohexane (C6F14) isomers.
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    • Compound 14 was identified by comparison of spectroscopic data of the debenzylated products (melibiose and allolactose) with those of authentic samples: K. Bock, C. Pedersen, H. Pedersen, Adv. Carbohydr. Chem. Biochem. 1983, 42, 193; K. Ajisaka, H. Fujimoto, H. Nishida, Carbohydr. Res. 1988, 180, 35.
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    • Compound 14 was identified by comparison of spectroscopic data of the debenzylated products (melibiose and allolactose) with those of authentic samples: K. Bock, C. Pedersen, H. Pedersen, Adv. Carbohydr. Chem. Biochem. 1983, 42, 193; K. Ajisaka, H. Fujimoto, H. Nishida, Carbohydr. Res. 1988, 180, 35.
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    • note
    • The anomer ratio of compound 17 (at the newly formed anomeric position) was determined to be α/β = 67:33 by NMR spectroscopic analysis.


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