Hexanes/acetonitrile: a binary solvent system for the efficient monosilylation of symmetric primary and secondary diols

Synthesis of C37‐Alkenones for Past Climate Reconstructions

“…The synthesis of the acetal‐protected 14‐bromotetradecanal 28 started from the commercially available 1,7‐heptanediol 4 (Scheme ), which was partially protected as tert ‐butyldimethylsilyl ether. In order to avoid a statistical distribution of mono‐, di‐ and un‐protected diol, a combination of a biphasic solvent system was employed in combination with a very slow addition of the silylating reagent. The alcoholic moiety was oxidised with the previously described methodology, although in low yields, presumably for an over oxidation caused by the presence of an excess of bleach.…”

Total Synthesis and Antimicrobial Activities of All Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide

“…(14-tert-Butyldimethylsilyloxy)tetradecan-1-ol (S1). 19 To a cooled (0 °C) solution of tetradecane-1,14-diol (817 mg, 3.55 mmol) in CH 3 CN (4.0 mL) and hexane (31.5 mL) were added Et 3 N (0.6 mL, 4.26 mmol) and TBSCl (561 mg, 3.72 mmol). The solution was stirred at 55 °C for 24 h. After cooling to room temperature, the reaction mixture was quenched with saturated aqueous ammonium chloride.…”

A high molar activity 18F-labeled TAK-875 derivative for PET imaging of pancreatic β-cells

“…The monoprotected diol 2 was synthesized following a literature procedure (Wilke et al 2014). A Mitsunobu coupling reaction was used to synthesize 3 in 70% yield.…”

“…3-(3-(tert-Butyl-dimethyl-silanyloxy)-propylsulfanyl)-propan-1-ol (2). The product 2 was prepared using a previously published method (Wilke et al 2014). 3,3′-Thiodipropanol (870 mg, 5.8 mmol) was added to acetonitrile (12 mL) and hexanes (48 mL).…”