The 4,6-O-[α-(2-(2-lodophenyl)ethylthiocarbonyl)benzylidene] protecting group: Stereoselective glycosylation, reductive radical fragmentation, and synthesis of β-D-rhamnopyranosides and other deoxy sugars

Organic Letters

Volumn 5, Issue 12, 2003, Pages 2189-2191

  Crich, David ^a   Yao, Qingjia ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIDENE DERIVATIVE; DEOXYSUGAR; ESTER DERIVATIVE; ETHER DERIVATIVE; PYRANOSIDE; THIOGLYCOSIDE;

ARTICLE; CHEMICAL REACTION; FRAGMENTATION REACTION; GLYCOSYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

BENZYLIDENE COMPOUNDS; DEOXY SUGARS; GLYCOSYLATION; PYRANS; RHAMNOSE; STEREOISOMERISM; THIOGLYCOSIDES;

EID: 0141854070     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034741r     Document Type: Article

References (27)

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3. Recent developments: (a) Abdel-Rahman, A. A.-H.; Jonke, S.; El Ashry, E. S. H.; Schmidt, R. R. Angew. Chem., Int. Ed. 2002, 41, 2972. (b) Kim, K. S.; Kim, J. H.; Lee, Y. J.; Park, J. J. Am. Chem. Soc. 2001, 123, 8477.
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6. β-D-Rhamnosides are found in the repeating unit of the antigenic exopolysaccharide common to Escherichia hermannii ATCC 33650 and 33652 isolated from human wounds, sputum, lungs, and stools: Beynon, L. M.; Bundle, D. R.; Perry, M. B. Can. J. Chem. 1990, 68, 1456. The ultimate challenge in terms of β-D-rhamnoside synthesis is probably the antigenic polysaccharide from Escherichia hermannii ATCC 33651, a β-D-rhamnan: Perry, M. B.; Richards, J. C. Carbohydr. Res. 1990, 205, 371.
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