Glucitol acetate

Fig. 18. Separation of glucitol derivatives labeled with aminobenzonitrile (ABN), obtained from methyl starch by capillary electrophoresis (CE/UV, top) and from glucitol acetates obtained from methyl cellulose by gas chromatography (GLC/FID, bottom xylitol = internal standard).

Glucitol D-Glucitol. See Sorbitol D-Glucitol, acetate. See Sorbityl acetate D-Glucitol, bis-0-((4-methylphenyl) methylene)-. See Di (p-tolylidene) sorbitol D-Glucitol, bis-o-(phenylmethylene)-. See Dibenzylidene sorbitol D-Glucitol, l-deoxy-l-(methylamino)-. See... 

CAS 39346-74-2 EINECS/ELINCS 254-423-2 Synonyms Acetic acid, sorbitol ester D-Glucitol, acetate... 

Trade Names Aqua Pro WG Glicerol. See Glycerin Glucitol D-Glucitol. See Sorbitol D-Glucitol, acetate. See Sorbityl acetate... 

GC separation of the acetate derivatives rhamnitol, fucitol. ribi-tol, arabinitol, mannitol, galacitol, glucitol, and inositol... 

The simple cleavage of lactones 1 or 2 with alcohol and acid has not been reported. However, when 1 is treated with benzaldehyde diethyl acetal and hydrochloric acid, ethyl 3,5 4,6-di-0-benzylidene-L-gulonate (47) is formed in >90% yield.77,78 No other isomers were observed, and other acetals of benzaldehyde, as well as aliphatic aldehydes, afford similar products in good yield.77 D Addieco prepared36 similarly protected derivatives of L-gulonic acid by oxidation of l,3 2,4-di-0-ethylidene-D-glucitol (15), followed by esterification of the resulting acid with diazomethane. 

Polyhydroxy compounds are known to form borate complexes that can interfere with the subsequent acetylation step. In essence, two methods of acetylation are employed. In one, the conditions are sufficiently vigorous that borate complexes are cleaved during the acetylation, and, in the second, the complexes are decomposed prior to acetylation. In one example of the former method, the crude, dry alditols were refluxed for 4 hours with a mixture containing equal amounts of acetic anhydride and pyridine ( 1 ml/100 mg), and the cooled solution was injected directly into the gas chromatograph.217 The effect of borate on the rate of acetylation of glucitol by this... 

In connection with the structure of glycoproteins, Lloyd and Kabat studied the separation of six alditol acetates,452 and Kim and coworkers57 examined the separation of L-fucitol, D-glucitol, D-manni-tol, and galactitol. Alditol acetates have been used in studies on... 

The configuration at C-2 was established by comparison with the optical activities of 1,5-anhydro-D-mannitol and -D-glucitol and the proton magnetic resonance (p.m.r.) spectra of their acetates.31(b) This reaction is useful for the preparation of C-2 substituted derivatives, but the configuration at C-2 of the products must then be established. 

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. 

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... 

This reaction was extended to 0-(o-nitrobenzylidene) derivatives of glycerol,67 D-mannitol,68 and D-glucitol.69 Some regioselectivity seems to have been observed, as two acetal groups [of the three for the tri-O-(o-nitrobenzylidene) derivatives of D-mannitol and D-glucitol] were found to have reacted. The identity and the structure of the photo-... 

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. 

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