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  • Title: Synthesis of 3,6-dideoxy-3-(methylamino)hexoses for g.l.c.-m.s. identification of Rhizobium lipopolysaccharide components.
    Author: Hollingsworth RI, Hrabak EM, Dazzo FB.
    Journal: Carbohydr Res; 1986 Oct 15; 154():103-13. PubMed ID: 3791291.
    Abstract:
    A direct synthetic route from methyl alpha-D-glucopyranoside to 3,6-dideoxy-3-(methylamino)hexoses having the D-gluco, D-galacto, and D-manno configurations has been developed. Methyl alpha-D-glucoside was converted into the 4,6-O-benzylidene-2,3-di-O-tosyl derivative, which was then transformed into the 4-O-benzyl-6-deoxy 2,3-ditosylate (5) by successive reductive cleavage of the acetal ring, iodination, and reduction. The intermediate 5 was readily converted into the allo 2,3-epoxide, which yielded the pivotal intermediate methyl 4-O-benzyl-3,6-dideoxy-3-(methylamino)-alpha-D-glucopyranoside (7) by cleavage of the oxirane ring with methylamine. The amino compound 7 can be directly converted into the derivatized galacto and manno derivatives for mass-spectrometric identification by selective inversion at C-4 and C-2, respectively, followed by hydrolysis, reduction, and acetylation.
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