Mannitol hexaacetate

Reference alditol acetates elute from the BPX-70 column in the following order erythritol triacetate, 2-deoxyribitol tetraacetate, rhamnitolpentaacetate, fucitolpentaacetate, ribitol pentaacetate, arabinitol pentaacetate, xylitol pentaacetate, 2-deoxyglucitol hexaacetate, allitol hexaacetate, mannitol hexaacetate, galactitol hexaacetate, glucitol hexaacetate, and rnyo-inositol hexaacetate. Their identification can be verified by using individual standards. 

Dichlorohydrins, as a rule, are readily obtained by direct reaction although some are easily converted to anhydro polyols. Higher halohydrins can only be obtained by indirect means. Thus, erythritol tetraacetate was converted to a tetrabromohydrin, m.p. 118 , by hydrobromic acid in glacial acetic acid at 150°C., whereas mannitol hexaacetate could not be carried beyond the pentabromo stage at 130-140 (94)- Mannitol was converted... 

Alditols, Cyclitols and Derivatives Thereof. - 2,5 3,4-Dianhydro-D-altritol, 2,5-aohydro-3,4-0-(l,2-ethanediyl)-D mannitol, pentaerythritol tetraacetate, ribitol tetraacetate, xylitol tetraacetate, D-arabinitol tetraacetate, D, L-arabinitol tetraacetate, 2,4 3,5-di-0-isopropylidene-D-mannitol, 2 hexa-O-acetyl-D-mannitol, allitol hexaacetate, D-mannitol hexaacetate, D, L-mannitol hexaacetate, D-iditol hexaacetate, D, L-iditol hexaacetate, D, L-glucitol hexaacetate, D, L-altritol hexaacetate, L-galacto-D-galacto-decitol (which is C2-symmetric), 5 6-0-benzyl-2,3-0-[(S)-caniphanylidene]-l,4,5-tris-0-pivaloyl-D-myo-inositol, 6D-3,6-di-0-benzyl-l-0-[(S)-camphanyl]-2-deoxy-2,2-difluoro-4,5-0-isopropylidene- y< -inositol, cyclopentane 28. ... 

Conversion to acetates, trifluoroacetates (178), butyl boronates (179) trimethylsilyl derivatives, or cycHc acetals offers a means both for identifying individual compounds and for separating mixtures of polyols, chiefly by gas—Hquid chromatography (glc). Thus, sorbitol in bakery products is converted to the hexaacetate, separated, and determined by glc using a flame ionisation detector (180) aqueous solutions of sorbitol and mannitol are similarly separated and determined (181). Sorbitol may be identified by formation of its monobensylidene derivative (182) and mannitol by conversion to its hexaacetate (183). 

Following the observation that benzyl ethers are cleaved by acetic anhydride in the presence of sulfuric acid or perchloric acid, Allerton and Fletcher S extended the work to carbohydrate systems. 2,5-Di-O-benzyl-l,3 4,6-di-0-methylene-D-mannitol (12) gave 1,3,4,6-tetra-0-acetyl-2, 5-di-O-benzyl-D-mannitol in the presence of 0.09% of sulfuric acid, but, with 2.4% of the acid, the hexaacetate was formed. With 1,6-di-O-benzyl-2,4 3,5-di-0-methylene-L-iditol (13), brief acetolysis gave the di-0-acetyl-di-O-methylene derivative longer treatment gave the hexaacetate. 

In studies on levans, n-fructose, after reduction with sodium boro-deuteride, was analyzed, as the alditol acetates, by g.l.c. n-Glucitol-2-d and D-mannitol-2-df hexaacetates were obtained, and their identities, and the position of the deuterium atoms, were confirmed by m.s. 

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