Synthesis of C-glycopyranosyl compounds by a palladium-catalyzed coupling reaction of 1-tributylstannyl-D-glucals with organic halides.
1-Tributylstannyl-D-glucals, prepared from the corresponding 1-phenylsulfonyl-D-glucals, were coupled efficiently to various organic halides in the presence of a palladium(0) catalyst. This mild reaction is specially useful for the preparation of 1-C-aryl-D-glucals and compatible with unprotected hydroxy groups or hindered aromatic bromides. It has been shown that the resulting 1-C-aryl(alkyl)-D-glucals are suited for further synthetic manipulation of the enol ether group, including stereoselective hydrogenation, hydroboration-oxidation, or epoxidation. All compounds formed resulted from the attack of the alpha-face of the glucal derivatives by the reagent. The reaction, extended to 1,3-, 1,4-di-, and 1,3,5-tri-bromobenzenes, leads to the corresponding symmetrical di-(tri)-C-glucosylbenzenes. Finally, a sequential di-C-glucosylation of 1,3-dibromobenzene with two different 1-stannylated glucals was obtained.
Dubois
E
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Laboratoire de Biochimie Structurale, URA 499, Université d'Orléans, France.
Beau
J M
JM
D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002125:Calcium Gluconate / Q000031:analogs & derivatives; D002240:Carbohydrate Sequence; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009942:Organometallic Compounds; D010165:Palladium; D014001:Tin
D000970:Antineoplastic Agents; D006027:Glycosides; D009942:Organometallic Compounds; D010165:Palladium; D014001:Tin; D002125:Calcium Gluconate