Synthesis of alpha,alpha-trehalose 2,3- and 2,3'-diesters with palmitic and stearic acid: potential immunoreactants for the serodiagnosis of tuberculosis.
Regioselective monoacylation, by the stannylation method, of 4,6:4',6'-di-O-benzylidene-alpha,alpha-trehalose with palmitoyl or stearoyl chloride afforded the 2-palmitate and 2-stearate of the diacetal, whereas partial diacylation led to the corresponding 2,3'-dipalmitate and 2,3'-distearate. Protection of the monoesters in the 2',3' positions by cyclizing silylation with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane, followed by acylation of the silyl ethers, gave the fully protected 2,3-dipalmitate, 2,3-distearate, and 2-palmitate-3-stearate. Small proportions of other isomers and triesters were also produced in these reactions. Desilylation and debenzylidenation of the diesters finally furnished 2,3- and 2,3'-di-O-palmitoyl-2,3- and 2,3'-di-O-stearoyl-, and 2-O-palmitoyl-3-O-stearoyl-alpha,alpha-trehalose.
Baer
H H
HH
Department of Chemistry, University of Ottawa, Ontario, Canada.
Wu
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D000937:Antigen-Antibody Reactions; D002240:Carbohydrate Sequence; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D006017:Glycolipids / Q000737:chemistry / Q000276:immunology; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D019308:Palmitic Acid; D010169:Palmitic Acids / Q000737:chemistry* / Q000276:immunology; D012698:Serologic Tests; D013229:Stearic Acids / Q000737:chemistry* / Q000276:immunology; D014199:Trehalose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000276:immunology; D014376:Tuberculosis / Q000175:diagnosis
D004952:Esters; D006017:Glycolipids; D007202:Indicators and Reagents; D010169:Palmitic Acids; D013229:Stearic Acids; D019308:Palmitic Acid; C031183:stearic acid; D014199:Trehalose