Inositols from sugars

In 1953, Brown and Serro described61 the isolation and identification of galactinol and myo-inositol from the juice of the sugar beet (Beta... 

Variants of this reaction used to construct inositols were introduced by Prestwich [301] and Sinay [302]. These new methods have been reviewed elsewhere [303]. Additionally, a chapter of this book deals with methods of carbocyclization to form carbasugars from sugars. 

The trithiocarbonates may prove useful as intermediates for the synthesis of sugar dithiols from epoxides. Ring opening by reductive cleavage with lithium aluminum hydride gives excellent results with aliphatic and ahcyclic trithiocarbonates. When both carbon atoms are secondary, the product is a iraws-dithiol for example, cyclohexene oxide, which is converted into a irans-trithiocarbonate, gives, on reduction, cyclo-hexane-1,2-dithiol. The reaction has been used in the cyclitol series for the preparation of 1,2-dithio-neo-inositol and 1,2-dithio-ir-inositol, from 1,2-anhydro-alZo-inositol. The inositol trithiocarbonates show pronounced Cotton effects in their optical rotatory-dispersion spectra. 

Reviews have appeared on the synthesis of inositols, carba sugars, conduritols and amino conduritols utilizing the non-carbohydrate sources of benzene cis-diols, quinic acid and Vogel s naked sugar methodology. Other reviews on the preparation of cyclophellitol and ep/-cyclophellitol from glycals and the use of D-glyceraldehyde as a chiral precursor in Diels-Alder and 1,3-dipolar cycloaddition approaches to carbocyclic derivatives have also been reported. 

Inositol, which has been known as a chemical compound since 1850, is widely distributed in foods and closely related to glucose. It was first commonly called muscle sugar and given the name inositol from two Greek roots inos, meaning sinews and -ose, the suffix for sugars. 

The deoxyinositols (quercitols, cyclohexanepentols) are useful model compounds which display many of the physical and chemical properties of true deoxy sugars. Although (-b)-proto-quercitol, the best known isomer, was isolated from nature 118 years ago, no synthesis has been reported up until now. The synthesis here described is actually that of the (-)-enantiomer, starting with (-)-inositol however, identical procedures applied to the readily available ( + ) or dl-inositol would give (- -) or DL-proto-quercitol, respectively. The natural occurence of, )-proto-quercitol has... 

The power of the new spectrometer to reveal configurations of difficult cyclitols or sugars was first tested with mt/o-inositol (2), using deuterium oxide as solvent. At 60 or 100 MHz. the one equatorial and five axial protons appear to have different chemical shifts as shown by Lemieux in 1956 with a 40 MHz. instrument (14,15). However, since the five-proton axial signal could not be resolved, one could probably not have assigned the configuration 2 (which was already known from laborious chemical correlations extending over many years.)... 

Ubiquitous in seeds is phytic acid, the hexaphosphate ester of inositol, which has been isolated from cucurbit seeds (57). Small amounts of free sugars and terpenoid glycosides (cucurbitacins) are also present (58-60), but starch is absent (1, 1). Cellulosic cell wall materials comprise the remaining carbohydrate content. 

N.A. Allantoin, sugars, leucine, tyrosine, arginine, inositol." The pods are diuretic, stimulating urine flow, and flushing toxins from the body. 

An illustration drawn from the field of sugar chemiatjy involves addition of toluene-jP Sulfomo acid to the inositol derivative1388 shown in Eq. (783). 

Now, all the predicted sixteen stereoisomers of racemic pseudo-sugars have been synthesized and their physical constants are listed in Table 1. The first three pseudosugars 9,14 and 17 have been synthesized by McCasland and his coworkers. The two pseudo-sugar pentaacetates 28 and 29 were prepared from myo-inositol. All the remaining eleven pseudo-sugars have been synthesized from the Diels-Alder adduct... 

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