1.6- Anhydro-D-galactose

Klemer and Kohla have reported further remarkable transformations of sugar acetals on treatment with alkyl lithium reagents. 1,6-Anhydro-D-galactose derivative (38) gave the cyclitol (39), In 85% yield for R=Bu, while the 1,6-anhydro-D-mannose derivative (ll0)... 

Closely allied with this is the preparation of chiral components for the purpose of making stereochemical correlations. A notable example (although not of an acyclic entity) is found in the work of Belleau (Scheme 5) related to the potent cholinergic methiodide (11). In the pursuit of determining the relative and absolute configurations of members of this series, 1,6-anhydro-D-galactose (12) was degraded to the chiral dioxolane (13) 94). 

The squalestatin (or zaragozic acid) class of squalene synthase inhibitors presents an interesting challenge to the synthetic chemist and studies directed towards this goal have been reported. 1,6-Anhydro-D-galactose has formed the basis of the synthesis of 107 and the more advanced intermediate 108 (sugar numbering is shown). ... 

R. R. Schmidt, J. Michel, and E. Rucker, Synthese von 1,6-Anhydro-D-glucose- und -D-galactose-Derivaten. Herstellung des 1-Desoxynojirimycins, Liebigs Ann. Chem., (1989) 423-428. 

The first synthesis of 2,3,4-trimethyl-D-galactose, which had previously been isolated from the hydrolysis products of methylated galac-tosans, was achieved by McCreath and F. Smith.20 1,6-Anhydro-D-galactopyranose, treated with dimethyl sulphate and alkali, underwent easy methylation and the resulting crystalline 2,3,4-trimethyl-l,6-anhydro-D-galactopyranose was conveniently hydrolyzed to the free sugar hydrate. 

The mechanism by which the 1,4-anhydro-D-galactose derivative (10) is formed on reaction of the, 6-dimesylate (11) with azide tij... 

From Rodriguez, Merino, Pujol, Damonte, Cerezo, Matulewicz 2005. Yields are given as percentages of the total recovered for F1-F3 (65.1 %). Small quantities of Glc and Man were detected in F1-F3. Only 3,6-anhydro-D-galactose was detected by NMR spectroscopy for F3 and F3T3 this was confirmed by an analytical procedure. Considering Xyl, Glc, and Man as contaminants. Soluble in 2.0 M KCl. 

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