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Synthesis of α,α-trehalose 2,3- and 2,3′-diesters with palmitic and stearic acid: potential immunoreactants for the serodiagnosis of tuberculosis

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
238
Identifiers
DOI: 10.1016/0008-6215(93)87014-j

Abstract

Abstract Regioselective monoacylation, by the stannylation method, of 4,6:4′,6′-di- O-benzylidene-α,α-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-α,α-trehalose.

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