Synthesis of monoacid 2,3-diacyl-sn-glycerols via 1,6-ditrityl-d-mannitol |
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| Authors: | J.A. Virtanen J.R. Brotherus O. Renkonen M. Kates |
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| Affiliation: | 1. Department of Chemistry, University of Helsinki, Vuorikatu 20, 00100 Helsinki 10 Finland;2. Department of Biochemistry, University of Helsinki, Unioninkatu 35, 00170 Helsinki 17 Finland;3. Department of Biochemistry, University of Ottawa, Ottawa, K1N 9B4 Canada |
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| Abstract: | Stereochemically pure 2,3-dipalmitoyl-sn-glycerol and 2,3-dioleoyl-sn-glycerol were prepared in an overall yield of 20% by a new and facile method starting from D-mannitol. The synthetic intermediates were 1,6-ditrityl-D-mannitol (1), 1-trityl-sn-glycerol (2), and 1-trityl-2,3-diacyl-sn-glycerol (3). The key reaction was the oxidation of 1 with lead tetraacetate followed by reduction with sodium borohydride. The product (2) was readily separated from the only byproduct, tritylethyleneglycol. |
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