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Synthesis of a Library of Propargylated and PEGylated α-hydroxy Acids Toward "Clickable" Polylactides via Hydrolysis of Cyanohydrin Derivatives

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

J Org Chem. 2014 Oct 17;79(20):9546-55.

PMID: 25255205

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS71144	Poly(L-lactide), propargyl terminated			Price

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