Date of Award

2021

Document Type

Open Access Master's Thesis

Degree Name

Master of Science in Chemistry (MS)

Administrative Home Department

Department of Chemistry

Advisor 1

Shiyue Fang

Committee Member 1

Rudy Luck

Committee Member 2

Marina Tanasova

Committee Member 3

Tarun Dam

Abstract

Stepwise synthesis of monodisperse polyethylene glycols (PEGs) and their derivatives usually involves using an acid-labile protecting group such as DMTr and coupling two PEG moieties together under the basic Williamson ether formation conditions. Using this approach, each elongation of PEG is achieved in three steps – deprotection, deprotonation, and coupling – in two pots. Here, we report a more convenient approach for PEG synthesis featuring the use of a base-labile protecting group such as the phenethyl group. Using this approach, each elongation of PEG can be achieved in only two steps – deprotection and coupling – in one pot. The deprotonation step and the isolation and purification of the intermediate product after deprotection using existing approaches are not needed when the new one-pot approach is used. Because stepwise PEG synthesis usually requires multiple PEG elongation cycles, the new PEG synthesis method is expected to significantly lower PEG synthesis cost and reduce the use of harmful solvents and other chemicals.

Available for download on Saturday, July 23, 2022

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