D-Sorbose

D-Sorbose Sugar Phosphates by Enzymatic Addition of Dihydroxyacetone Phosphate to Aldehydes Typical Procedure8 ... 

Some examples will illustrate the applicability of this generalization in so far as it concerns alkaline scission. 5,6-Anhydro-l,2-isopropylidene-D-glucofuranose with alcoholic sodium hydroxide gives a mixture of isopropylidene-D-glucose and isopropylidene-L-idose. The latter results from inversion on C5, the former presumably by inversion on the non-asymmetric C6.7 3,4-Anhydro-l,2-isopropylidene-D-psicose (or allu-lose17) (XX) when treated with sodium hydroxide yields a mixture of products among which 1,2-isopropylidene-D-fructose (XIX) was detected (in the representations inversions are denoted by circles above the arrows and the carbons inverted are noted below the arrows). With sodium methoxide, however, l,2-isopropylidene-4-methyl-D-sorbose (XXI) is the chief product and results from inversion on C4.1S... 

D-Glucose-l-D-fructoside + D-sorbose, D-glucose- l-i/-sorboside + D-fructose... 

L-Glucitol (n-gulitol), the enantiomorph of sorbitol, has been obtained by the action of sodium amalgam on D-gulonolactone or, along with D-iditol, on D-sorbose. ... 

D-Glucitol (Sorbitol or Hexanhexol), HOCH2(CHaOH)4CH2OH raw 182.17, ndls (with lA or 1 w), tnp about ll0°(dry), -100° or less (with w), very hygr when dry sol in w hot ale. Found in various fruits prepd by sodium amalgam reduction of d-sorbose or by pressure hydrogenation of dextrose with Ni catalyst. Used far prepn of ascorbic acid (Vitamin C), for synthesis of resins, surface-active agents, varnishes, syrups, cosmetic creams aod for explosive Sorbitol Hexanitrate... 

The substrate spectrum of SuSyl from yeast is well documented for a variety of acceptors [24, 29, 30]. In the series of ketoses we concluded that SuSyl favors the 3S,4R configuration because L-sorbose 4 and D-xylulose 5 are accepted and D-tagatose 6, D-psicose 7, and D-sorbose 8 are not substrates (Fig. 2.2.6.1 and... 

The action of mixed acid on d-sorbose at 15° yields sorbosan trinitrate, C6H702(0N02)3, a crystalline substance which melts not sharply at 40-45°. 

Ohle and Just112 have carried out the following sequence 1,2-isopro-pylidene-D-fructopyranose 3-p-toluenesulfonate —> l,2-isopvopylidene-3,4-anhydro-D-psicose —> l,2-isopropylidene-4-methyl-D-sorbose (VII), ([a]D -81.6°). Since the introduction of a methyl group does not alter greatly the specific rotation, it is to be expected that the parent 1,2-iso-... 

D-Sorbose (pseudotagatose), which has been designated i-sorbose in the early literature, was obtained along with other products by warming D-galactose with very dilute potassium hydroxide21 or calcium hydroxide.22 The historical aspects of the change of the name from Z-sorbose to D-sor-bose have been discussed by Hudson.23... 

The realized transformation of D-galactose to D-sorbose, which would involve enolization between carbons 2 and 3, is not an isolated case of this... 

By treatment of D-gulose (XVII) or D-idose (XVIII) with warm aqueous barium hydroxide solution Van Ekenstein and Blanksma were able to isolate D-sorbose (II) with a melting point of 165° and [< ]d + 42.9° in water. The aldoses were prepared from D-gulonic and D-idonic lactones obtained by the cyanohydrin synthesis from D-xylose. 

Recently Gatzi and Reichstein28 have prepared D-sorbose by refluxing D-gulose with pyridine and by the action of very dilute potassium hydroxide on D-galactose. The product of the latter reaction was contaminated with a little D-tagatose. 

A mixture of ketohexoses, from which D-sorbose and D-fructose were isolated in crystalline condition,29 was also obtained by barium hydroxide treatment of D-glyceraldehyde alone, or with dihydroxyacetone. 

In a series of reactions similar to those used in the preparation of D-psicose, Wolfrom, Olin and Evans30 synthesized D-sorbose (II) from D-xylonyl chloride tetraacetate (XIX) via the l-desoxy-l-diazo-fcefo-D-sorbose tetraacetate (XX) and fcefo-D-sorbose pentaacetate (XXI). 

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