- An efficient and practical preparation of a potent low-affinity na+-dependent glucose cotransporter (SGLT2) inhibitor, sergliflozin etabonate
-
The development of an efficient and practical process for the preparation of Sergliflozin etabonate (1), a prodrug of a novel selective low-affinity Na+-dependent glucose cotransporter (SGLT2) inhibitor, Sergliflozin (2), is described. Its development required a suitable process for large-scale manufacturing. We established a chromatography-free approach for 2-[(4-methoxyphenyl)methyl]phenol (5), the efficient O-glycosylation of 5 with penta-O-acetyl-β-D-glucopyranose (7) without using a trichloroacetimidate intermediate (9), and efficient reaction conditions to introduce an ethoxycarbonyl group onto the primary alcohol of 2 with high selectivity. This process provided 1 with a 45% overall yield from anisole (10).
- Kobayashi, Masahiro,Isawa, Hidetoshi,Sonehara, Junichi,Kubota, Minoru
-
p. 1599 - 1613
(2016/10/12)
-
- Highly selective primary alkoxycarboxylation and esterification of unprotected pyranose derivatives mediated by scandium(III) triflate catalysis
-
A highly selective method for the alkoxycarboxylation and acylation of primary alcohols of pyranose derivatives is described. The reaction is high yielding and proceeds under mild conditions with 0.15-1 mol-% Sc(OTf) 3 used in combination with anhydrides or pyrocarbonates at 40-50 °C. Selectivities observed for alkoxycarboxylation of unprotected pyranose derivatives are > 95 and this constitutes a significant advantage over existing methods. Mechanistic implications, including the role of steric demand and metal-heteroatom coordination are also discussed.
- McClure, Michael S.,Berry, Malcolm B.,Caine, Darren,Crawford, Claire,Crump, Brian C.,Glover, Bobby N.,Kedia, Sandeep B.,Millar, Alan,Mitchell, Mark B.,Nichols, Christopher J.,Patterson, Daniel E.,Powers, Jeremiah
-
supporting information; experimental part
p. 3561 - 3565
(2012/07/27)
-
- Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing the same
-
The present invention relates to glucopyranosyloxybenzylbenzene derivatives represented by the general formula: wherein P represents a group forming a prodrug; and R represents a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower al
- -
-
-
- GLUCOPYRANOSYLOXYBENZYLBENZENE DERIVATIVES AND MEDICINAL COMPOSITIONS CONTAINING THE SAME
-
The present invention relates to glucopyranosyloxybenzylbenzene derivatives represented by the general formula: wherein P represents a group forming a prodrug; and R represents a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower al
- -
-
-