ISSN:
0170-2041
Keywords:
C-Saccharides
;
C-Glycosides
;
1-Lithiogalactal
;
Vinyllithium
;
Glucose, C-formyl-
;
Carbohydrates
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
4-C-Formylglucopyranoside 9 was readily obtained from 4-O-unprotected glucose derivative 4 in four steps, each step giving a high product yield. Reaction with 1-C-lithiated 2-phenylsulfinyl-D-galactal 10 as nucleophile furnished C-disaccharide intermediates 11a and 11b as diastereoisomers. Ensuing removal of the phenylsulfinyl group with Raney nickel and regio- and diastereospecific 2b-hydrogen and 3b-hydroxy transfer afforded β(1-4)-connected C-lactosides 13a and 13b, respectively; their structures were deduced from derivatives 14a, b and 16a, b on the basis of 1H-NMR data. Hydrogenolytic O-debenzylation of 13a and 13b afforded hydroxymethylene-bridged C-lactose 2a and 2b, respectively. Regioselective O-benzylation of 13a gave preferentially 1b-O-unprotected derivative 17aa which furnished upon oxidation carbonyl-bridged C-lactose derivative 19. Deoxygenation at C-1b of 17aa and subsequent hydrogenolytic O-debenzylation furnished methylene-bridged C-lactose 1.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419941004
