Glucitol periodate oxidation

Lemer (29) reported a simple synthesis of L-erythrose that involves 2,3-di-O-isopropylidene-D-gulono-1,4-lactone (7b) as a key intermediate. Reduction of the lactone group of 7b with sodium borohydride, followed by periodate oxidation of the L-glucitol derivative, afforded 2,3-O-isopropy-lidene-L-erythrose. The free sugar may be readily obtained by acidic hydrolysis of the latter. 

Oxepane (seven-membered) rings (1,6-anhydrohexitols)52 have been prepared from the 3,4-isopropylidene acetals of D-mannitol, D-glucitol, and L-iditol, by way of alkaline hydrolysis of the corresponding 1,2 5,6-dianhydrides. The ring structures of the products were established through periodate oxidation and lead tetraacetate oxidation the requisite amount of formic acid was produced, and 3 equivalents of lead tetraacetate were consumed. No inversions at any of the asymmetric centers were involved in the reactions conducted, so the oxepanes had retained the configurations of the starting hexitols. 

In the synthesis of 1,6-anhydro-D-glucitol, at least, a 2,6-anhydride is a byproduct.53 Its structure was assigned on the basis of its i.r. spectrum, in comparison with those of the 1,6- and 1,5-anhydro-D-glucitols, and the fact that no diglycolic acid was obtained after periodate oxidation followed by oxidation with hypobromite. 

Periodate oxidation of 2-acetamido-1,2-dideoxy-3,4-0-isopropylidene-D-glucitol (33) affords 4-acetamido-4,5-dideoxy-2,3-0-isopropylidene-aldehydo-c-xylose, which, on hydrolysis with acetic acid, gives31 the pyrrolidine 34. The same series of reactions was performed31" on the... 

Preparation. L-Xylose has been prepared by periodate oxidation of 2,4-0-benzylidene-D-glucitol followed by acid hydrolysis of the benzylidene group.53... 

A micro method for determining the structures of substituted 2-acetamido-2-deoxy-D-galactitol and -glucitol in glycoproteins, etc., has been reported. Aminodeoxy[ H]alditols resulting from periodate oxidation, reduction with sodium borotritide, and hydrolysis of nmole amounts of substituted 2-acetamido-2-deoxyalditols were separated by t.l.c. and detected by autoradiography. 

The Lewis acid-controlled addition of allyltrimethylsilane to various L-xylose derived acetals 16 afford chelation or non-chelation products 17 or 18. In two cases in which 16 R=Ph or C Yi -p-OMe was used in the presence of Bp3.0Et2, the tetrahydrofuran derivative 19 was obtained. The synthesis of compounds 16 are effected by way of periodate oxidation of appropriate alkylidene D-glucitols. 

The mild periodate oxidation of 3- and 6-O-substituted 2-acetamido-2-deoxy-D-galactitols and 4- and 6-O-substituted D-glucitols have been studied, and the major sites of oxidation shown as expected to be threo-diol moieties. The products were characterized by ms of thin layer chromatography samples of the corresponding 1,2-di-0-palmitoyl-sn-g/ycerD-3-phosphoethanolamine derivatives. 

Anhydroxylitol has been oxidized to give a sirup, characterized by oxidation to the strontium salt of the corresponding dicarboxylic acid. 1,5-Anhydro-D-glucitol (polygalitol) and 1, /)-anhydro-D-mannitol (styra-citol) have been oxidized with periodate, and then, further, to the corresponding strontium salt. ... 

Trioses and tetroses have been separated as their trimethylsilylated oximes by g.l.c. mass-spectral data for these derivatives were also recorded. Mixtures of xylitol, arabinitol, mannitol, glucitol, and maltitol have been separated efficiently by h.p.l.c. of the corresponding 4-nitrobenzoates. Alditols have been determined in the presence of neutral sugars by oxidation with acidified sodium periodate and colorimetric measurement of the formaldehyde released. G.l.c. retention data have been reported for the TMS derivatives of a large number of aldonic acids and their lactones and aldaric acids. ... 

The structures of many methylene sugar derivatives have not been determined, but those of many of the alditol derivatives are known. The greater ease of acetolysis of methylene groups attached to primary hydroxyls over those attached to secondary hydroxyls, has been of considerable value in the elucidation of the structures of these compounds by Hudson and co-workers (96), Thus the linkages at carbons 1 and 6 of 1,3 2,4 5,6-tri-O-methylene-D-glucitol are cleaved with sulfuric acid in acetic anhydride and acetic acid as shown in the formulas. The structure of the mono-0-methylene-D-glucitol is demonstrated by its oxidation with periodic acid... 

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