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Optically Active Monoacylglycerols: Synthesis and Assessment of Purity
Author(s) -
Chen ChaoYuan,
Han WeiBo,
Chen HuiJun,
Wu Yikang,
Gao Po
Publication year - 2013
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/ejoc.201300247
Subject(s) - chemistry , alkyl , hydrolysis , solubility , specific rotation , combinatorial chemistry , reactivity (psychology) , organic chemistry , medicine , alternative medicine , pathology
Despite their simple structures, synthesis of 1(or 3)‐acyl‐ sn ‐glycerols remains a challenge that cannot be ignored because of facile acyl migrations, which not only complicate the synthesis but also make direct GC or HPLC analysis unfeasible. Assessment of the optical purity of monoacylglycerols has, to date, relied almost exclusively on specific rotation data, which are small in value and thus insensitive to impurities. Now, a simple means to “magnify” the small specific rotations has been found, along with practical methods for the measurement of both 1,2‐ and 1,3‐acyl migrations, which offer a convenient and straightforward alternative to Mori's NMR analysis of Mosher esters. With the aid of these methods, a range of conditions for deacetonide removal were examined en route to the synthesis of two natural monoacylglycerols. Refined hydrolysis conditions, along with useful knowledge about the solubility and reactivity of substrates with an ultra long alkyl chain are also presented.