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Original Synthesis of Linear, Branched and Cyclic Oligoglycerol Standards
Author(s) -
Cassel Stephanie,
Debaig Catherine,
Benvegnu Thierry,
Chaimbault Patrick,
Lafosse Michel,
Plusquellec Daniel,
Rollin Patrick
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200103)2001:5<875::aid-ejoc875>3.0.co;2-r
Subject(s) - chemistry , regioselectivity , organic chemistry , branching (polymer chemistry) , heteroatom , combinatorial chemistry , ring (chemistry) , catalysis
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.