Inositol chemistry

The preparation of L-cAirt -inositol 2,3,S-trijdiosphate from L-quebrachitol has been reported/ The synthesis uses the conunercially available phosphitylating agent diethylchlorophosphine for the first time in inositol chemistry. 

Inositol Phosphates Their Chemistry, Biochemistry and Physiology, by D.J. Cosgrove... 

Cosgrove, D.J. "Inositol Phosphates Their Chemistry, Biochemistry, and Physiology" Elsevier Scientific Publishing Company New York, 1980. 

This process (also known as the Ferrier II Reaction ) has proved to be of considerable value for the efficient, one-step conversion of 5,6-unsaturated hexopyranose derivatives into functionalized cyclohexanones useful for the preparation of such enantiomerically pure compounds as inositols and their amino, deoxy, unsaturated and selectively O-substituted derivatives, notably phosphate esters. In addition, the products of the carbocyclization have been incorporated into many complex compounds of interest in biological and medicinal chemistry. ... 

The redox and complexation chemistry of alditol/Cr(VI) systems64 and the my<9-inositol/Cr(VI) system65 has been reported. In the first case, when an excess of the alditol over Cr(VI) is used, the secondary OH groups are inert to oxidation, and alditols are selectively oxidized at the primary OH group to yield the aldonic acid as the only oxidation product. The corresponding reaction involves a Cr(VI) —> Cr(V) —> Cr(III) reduction pathway, and the relative rate of each step depends on [H+] at... 

A review of our safety data to date shows that 107 patients have been treated with inositol. Of these, 61 have had full chemistry and hematology before and after inositol. Only two patients, both in the depression study, showed any changes in blood chemistry. Both showed a mild increase in blood glucose that disappeared on repeat in one but continued in the other several weeks after discontinuation of inositol. Total side effects were flatus in four patients, nausea in one, sleepiness in two, and insomnia in two. These side effects were similar to those reported in the placebo group. 

T. Postemak, The Cyclitols, Holden-Day, San Francisco, 1965, pp. 221-243 D. J. Cosgrave, Inositol Phosphates Their Chemistry, Biochemistry and Physiology, Elsevier, Amsterdam, 1980. 

C NMR has proven to be one of the most efficient spectroscopic methods for configurational and conformational investigations in carbohydrate chemistry. The signal assignments of mono-, di- and polysaccharides, inositols and polyols are carried out on the following basis ... 

The present review is to be regarded as a continuation of Fletcher s article1 the facts described therein will not be repeated here unless required for the understanding of recent developments. Because of the considerable expansion of cyclitol chemistry, it is not practicable to cover, as Fletcher did, all compounds of the cyclitol group. Only the inositols, the quercitols, and the inosamines, their derivatives, and some closely related compounds will be discussed the tetrahydroxycyclo-hexanes and -hexenes, and quinic and shikimic acids—on which subjects many important papers have appeared—are not reviewed here.3... 

The solvolysis of sulfonic esters, a much studied reaction, has not been applied in carbohydrate chemistry, presumably because most sugars are not stable enough to withstand the long heating required. Tosyl derivatives of inositols can, however, be solvolyzed in good yield. For example, 3-0-tosyl-feyo-inositol (5-0-tosyl-Zevo-inositol) (XLIV)—prepared from di-O-isopropylidene-fcvo-inositol (XXVIII) by tosylation and subsequent removal of the isopropylidene groups—affords aZZo-inositol when refluxed for... 

The recent reviews by Dangschat2(d) and Ballou2(e) have dealt extensively with cyclitols and related compounds in plants and micro-organisms. The emphasis in the following paragraphs is, therefore, on those aspects of the chemistry and biochemistry of the individual inositols which have not been discussed elsewhere. In particular, reports of the occurrence of cyclitols in plants are only included here if they are necessary for further discussion or if they are too recent to have been included in Dangschat s tables. 

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