ISSN:
0170-2041
Keywords:
D-Galactal
;
Galactopyranosides
;
Carbohydrates
;
Disaccharides
;
Saccharides
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Direct lithiation of the readily available 2-phenylsulfinyl-D-galactal 3S furnishes with aldehyde 8 as electrophile in a diastereocontrolled reaction the C-disaccharide intermediate 9. Subsequent removal of the phenylsulfinyl group with Raney nickel and diastereospecific 2b-hydrogen and 3b-hydroxy transfer provide the β(1→3)-connected C-disaccharide 11 in high yield. The structure of 11 was deduced from its derivative 12 on the basis of 1H-NMR data. Hydrogenolytic O-debenzylation gives compound 13, which is characterized as O-acetylated compound 14.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201161
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