Original Synthesis of Linear, Branched and Cyclic Oligoglycerol Standards

• Published in: European journal of organic chemistry Vol. 2001; no. 5; pp. 875 - 896
• Main Authors: Cassel, Stephanie, Debaig, Catherine, Benvegnu, Thierry, Chaimbault, Patrick, Lafosse, Michel, Plusquellec, Daniel, Rollin, Patrick
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag GmbH 01.03.2001; WILEY‐VCH Verlag GmbH; Wiley
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Polyglycerols; Science & Technology; Surfactants; Synthetic methods; standards; surfactants; D-GALACTOSE; ACID; GLYCEROL; polyglycerols; FUTURE; synthetic methods
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/1099-0690(200103)2001:5<875::AID-EJOC875>3.0.CO;2-R

A variety of authentic standards of linear, branched and cyclic oligomers of glycerol, with well‐defined structures and degrees of polymerisation from 2 to 5, have been efficiently synthesised. Linear oligomers were obtained by means of a convergent approach based on regioselective opening of bis(epoxides) with solketal; branched compounds were synthesised using oxidative cleavage of the corresponding anhydrohexitols as the key step. A 6‐exo‐trig halocyclisation reaction involving heteroatom‐tethered unsaturated alcohols permitted an efficient synthesis of the precursors of selected cyclic dimers; larger cyclic oligomers were prepared by two one‐pot Williamson reactions using a ditriflate derived from diglycerol. All these methodologies permitted further scaling up.