New deuterated oligo(ethylene glycol) building blocks and their use in the preparation of surface active lipids possessing labeled hydrophilic tethers

The Journal of Organic Chemistry
Robert J Faragher, Adrian L Schwan

Abstract

For the introduction of additional analysis protocols of tethered molecules, a method is presented to prepare functionalized, deuterated oligo(ethylene glycols) from ethylene glycol-d4. Partial oligomerization of ethylene glycol-d4 and conversion to ditosylates is accompanied by coupling reactions to prepare doubly benzyl protected oligo(ethylene glycols) with two to five repeating units. The tetramer bearing 16 deuteria was elaborated at both ends to eventually prepare 2,3-di-O-phytanyl-sn-glycerol-1-tetraethylene glycol-d,l-alpha-lipoic acid ester (DPTL), which bears a fully deuterated tetra(ethylene glycol) spacer group. Through linking of functionalized components, an analogue of DPTL possessing an octa(ethylene glycol) spacer group was prepared, both in deuterated and unlabeled form.

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Citations

Nov 6, 2013·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Hironao Sajiki
Jul 23, 2013·Biochimica Et Biophysica Acta·Lucia BecucciRolando Guidelli
Feb 22, 2017·Organic & Biomolecular Chemistry·Geoffray LericheJerry Yang
Aug 24, 2017·Chemistry : a European Journal·Ashok Khanal, Shiyue Fang
Jun 9, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Jay LeitchJacek Lipkowski
Mar 10, 2010·The Journal of Organic Chemistry·Kévin M JolyJames H R Tucker

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