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Paper | Regular issue | Vol 96, No. 4, 2018, pp.733-747
Published online, 28th March, 2018
DOI: 10.3987/COM-18-13881
An Efficient and Practical Synthesis of Remogliflozin Etabonate, a Potent Inhibitor of Low-Affinity Na+-Dependent Glucose Co-Transporter (SGLT2)

Masahiro Kobayashi* and Takayuki Ainai

*Quality Assurance, Kissei Pharmaceutical Co., Ltd, 19-48 Yoshino, Matsumoto-City, Nagano-Pref., Japan

Abstract

A practical process for the preparation of remogliflozin etabonate, a prodrug of the selective low-affinity Na+-dependent glucose co-transporter (SGLT2) inhibitor, remogliflozin, is described. We established a chemoselective synthetic route to 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5- methyl-3H-pyrazol-3-one and an efficient O-glycosylation of this compound with 2,3,4,6-tetra-O-pivaloyl-α-ᴅ-glucopyranosyl bromide. This synthetic process provided remogliflozin etabonate in a 39% overall yield from commercially available 4-isopropoxybenzaldehyde.