α-C-Glycosides via syn Opening of 1,2-Anhydro Sugars with Organozinc Compounds in Toluene/n-Dibutyl Ether.
The diastereoselective addition of organozinc species to 1,2-anhydro sugars in toluene/n-dibutyl ether solvent is reported. Compared to the existing methods, the reaction proceeds at 0 °C, and only a slight excess of nucleophile is required to achieve good yields. Scope was assessed with different O-protected glycals along with various nucleophiles (aryl, alkynyl). This methodology was applied to the synthesis of the α-anomer of canagliflozin.
Pharmaceutical Development and Manufacturing Sciences, Janssen Pharmaceutica , Turnhoutseweg 30, B-2340 Beerse, Belgium.
Simon
S
Wagschal
Pharmaceutical Development and Manufacturing Sciences, Janssen Pharmaceutica , Turnhoutseweg 30, B-2340 Beerse, Belgium.
Johan
J
Guilbaud
Pharmaceutical Development and Manufacturing Sciences, Janssen Pharmaceutica , Turnhoutseweg 30, B-2340 Beerse, Belgium.
Pauline
P
Rabet
Pharmaceutical Development and Manufacturing Sciences, Janssen Pharmaceutica , Turnhoutseweg 30, B-2340 Beerse, Belgium.
Vittorio
V
Farina
Pharmaceutical Development and Manufacturing Sciences, Janssen Pharmaceutica , Turnhoutseweg 30, B-2340 Beerse, Belgium.
Sébastien
S
Lemaire
D000480:Alkynes / Q000737:chemistry*; D000068896:Canagliflozin / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014050:Toluene / Q000737:chemistry*
D000480:Alkynes; C438934:C-glycoside; D004987:Ethers; D006027:Glycosides; D009005:Monosaccharides; D000068896:Canagliflozin; C053284:dibutyl ether; D014050:Toluene