2-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-1,3-dithiane

Abstract

In the title compound, C19H21ClOS2, the dithiane ring adopts a chair conformation. The dihedral angle between the benzene rings is 87.88 (4)°. In the crystal, inversion dimmers linked by pairs of C—H⋯O inter­actions occur.

Synthetic Strategies toward SGLT2 Inhibitors

“…An alternative approach was developed by the Pfizer Process Research Group (Scheme ). The key step of their improved stereoselective synthesis was the addition of aryl dithiane 102 (obtained in a seven-step process , ) to aldehyde 101 using n -BuLi in THF at low temperatures (Scheme ). Initially, diacetone-α- d -mannofuranose ( 99 ), which had been prepared from mannose by ketalization, was protected by silylation with TBDMSCl in the presence of imidazole.…”

“…The advanced aromatic intermediate 102 was prepared in seven linear steps in an overall yield of 6% (Scheme ). In the first step, intermediate 107 was converted to the corresponding acyl chloride, which then underwent Friedel–Crafts acylation in the presence of AlCl 3 in CH 2 Cl 2 to afford diaryl ketone 108. Next, radical bromination with N -bromosuccinimide (NBS) in the presence of azobis­(isobutyronitrile) (AIBN) in refluxing CCl 4 provided 5-bromomethanone 109 , which was reduced with Et 3 SiH and BF 3 ·Et 2 O in CH 3 CN/CH 2 Cl 2 to yield 110.…”

Stereoselective Synthesis of a Dioxa-bicyclo[3.2.1]octane SGLT2 Inhibitor

“…The new synthesis, exemplified by the preparation of 1 , is summarized in Scheme . Diastereoselective addition of the lithium anion derived from crystalline dithiane 2 to aldehyde 3 (readily available starting from diacetone-α- d -mannofuranose) at low temperature in THF produced intermediate 4 as a single diastereomer via Si face addition to the aldehyde…”