Large Scale Monotritylation of Water Soluble Compounds Containing Multiple Hydroxyl Groups

High‐Purity Discrete PEG‐Oligomer Crystals Allow Structural Insight

“…Two adaptations allowed us to greatly improve the outcome of our synthetic strategy. Firstly, use of monotrityl ether protection,37 in place of tert ‐butyl furnished substrates, such as 4 , with superior chromatographic separations. Secondly, with an empirical connection between presence of alkoxide and depolymerization established, subsequent coupling methods were designed to minimize reacting concentrations of alkoxide through slow addition of a solution of potassium tert‐ butoxide to the coupling partners, such as alcohols 4 or 7 and tosylates 5 or 12 in DMF.…”

High‐Purity Discrete PEG‐Oligomer Crystals Allow Structural Insight

“…Firstly, use of monotrityl ether protection, [37] in place of tert-butyl furnished substrates, such as 4, with superior chromatographic separations. Firstly, use of monotrityl ether protection, [37] in place of tert-butyl furnished substrates, such as 4, with superior chromatographic separations.…”

“…Two adaptations allowed us to greatly improve the outcome of our synthetic strategy. Firstly, use of monotrityl ether protection, [37] in place of tert-butyl furnished substrates, such as 4, with superior chromatographic separations. Secondly, with an empirical connection between presence of alkoxide and depolymerization established, subsequent coupling methods were designed to minimize reacting concentrations of alkoxide through slow addition of a solution of potassium tertbutoxide to the coupling partners, such as alcohols 4 or 7 and tosylates 5 or 12 in DMF.…”

Convenient Synthesis of a Polyester‐co‐Polyether Block for Assembling Biocompatible Hyperbranched Macromolecules

“…Two approaches to synthesize the compound 2 were tested: a) via monotrityl­ation of tetraethylene glycol followed by the etherification by Williamson reaction with sodium and allyl bromide, and the removal of trityle protective group ( 4 → 5 → 6 → 2 ); and b) by direct transformation of the excess of tetraethylene glycol by Williamson reaction with sodium and allyl bromide ( 4 → 2 ). In the first approach, the monotritylation of 4 was successfully carried out by a slightly modifying known protocol with 93% yield. The derivative 5 was then transformed into its alcoholate by reaction with metallic sodium.…”