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Issue 0, 1966
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Chemical transformations of αα-trehalose

G. G. Birch 

Abstract

αα-Trehalose reacts with acetaldehyde to form crystalline di- and hexa-O-ethylidene compounds analogous to the known compounds of methyl D-glucoside. Di-O-ethylidene-αα-trehalose can be mesylated and tosylated to form crystalline products. The time necessary for complete tosylation indicates that secondary hydroxyl groups are reacting. By analogy with D-glucose and methyl D-glucoside, the compounds are probably 4,6 : 4′,6′-di-O-ethyl-idene-αα-trehalose and 4,6 : 4′,6′-di-O-ethylidene-2,3 : 2′,3′-di-O-(oxydiethylidene)-αα-trehalose. The formation of these compounds lends support to the idea that the known glucopyranose rings in αα-trehalose are in the C1 conformation. The synthesis of 6,6-dideoxy-αα-trehalose is described.

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Article type: Paper
DOI: 10.1039/J39660001072
Citation: J. Chem. Soc. C, 1966,0, 1072-1074
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    Chemical transformations of αα-trehalose

    G. G. Birch, J. Chem. Soc. C, 1966, 0, 1072
    DOI: 10.1039/J39660001072

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