Synthesis of a library of propargylated and PEGylated α-hydroxy acids toward "clickable" polylactides via hydrolysis of cyanohydrin derivatives

Quanxuan Zhang, Hong Ren, Gregory L. Baker

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

A new simple and practical protocol for scalable synthesis of a novel library of propargylated and PEGylated α-hydroxy acids toward the preparation of "clickable" polylactides was described. The overall synthesis starting from readily available propargyl alcohol, bromoacetaldehyde diethyl acetal, and OEGs or PEGs was developed as a convenient procedure with low cost and no need of column chromatographic purification. The terminal alkyne functionality survives from hydrolysis of the corresponding easily accessible cyanohydrin derivatives in methanolic sulfuric acid. Facile desymmetrization, monofunctionalization, and efficient chain-elongation coupling of OEGs further enable the incorporation of OEGs to α-hydroxy acids in a simple and efficient manner. At the end, synthesis of allyloxy lactic acid indicates that an alkene group is also compatible with the developed method. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)9546-9555
Number of pages10
JournalJournal of Organic Chemistry
Volume79
Issue number20
DOIs
StatePublished - Oct 17 2014

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