D-Glucose diethyl thioacetal

A somewhat similar configurational correlation between (leva)-glyceraldehyde and (dexfro)-lactic acid has been made by Wolfrom, Lemieux, Olin and Weisblat.36 Reductive desulfurization of tetra-acetyl-2-methyl-D-glucose diethyl thioacetal (XXVII) and hydrolysis of the product gave 2-methyl-l-desoxy-D-glucitol (XXVIII) oxidation... [Pg.24]

D-Glucose diethyl thioacetal pentaacetate to l-desoxy-D-glucitol penta- ... [Pg.39]

Tetraacetyl-2-methyl-D-glucose diethyl thioacetal to tetraacetyl-2- 70% EtOH 5 hrs. ... [Pg.39]

Borate complexes have been utilized by Brigl and Griiner47 to effect partial esterification. Anhydrous D-glucose and metaboric acid dissolved in acetone give a complex which exhibits the analysis of a diborate. Reaction of the latter with an excess of benzoyl chloride gives 2,6-di-O-benzoyl-D-glucose (XL). D-Mannitol likewise forms a diborate, which produces the 1,6-di-O-benzoyl derivative (XLI) upon benzoylation. In the presence of boric acid, D-glucose diethyl thioacetal yields the 6-benzoate (XLII). In the non-aqueous medium the formation of complexes... [Pg.15]

Brigl and Muhlschlegel148 were able to isolate 3,4,5,6-tetra-O-benzoyl-D-glucose diethyl thioacetal from the thioacetal and benzoyl chloride in an aqueous solution of alkali. When the reaction is carried out in pyridine, both the tetra- and the penta-benzoate are obtained. The tetrabenzoate has been described as a convenient intermediate for the synthesis of 2-0-methyl-n-glucose and its derivatives.149 It is somewhat surprising that position 2 should exhibit this resistance to benzoylation, since preferential methylation occurs in this position. A benzoyl migration could possibly explain the anomalous observations. [Pg.36]

The Acetyl Group Migrations in D-Glucose Diethyl Thioacetal Tetraacetate, R. U. Lemieux and H. F. Bauer, Can. J. Chem., 32... [Pg.16]

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