Of carbohydrate boronates

Naming of carbohydrate boronates may be based on three principles (a), the central use of the ester heterocyclic rings 1,3,2-dioxaborolane (five-membered), 1,3,2-dioxaborinane (six-membered), and 1,3,5,2,4-trioxadiborepane (seven-membered, for example, 8 and 9) (b), the use of radical prefixes borylene (Chem. Abstr.) or boranediyl (I.U.P.A.C.) for /BH or (c), ester terminology. Thus, for example, according to these respective procedures, the glycerol derivative 10... 

It seems probable that a fundamental distinction may exist between the two methods available for the synthesis of carbohydrate boronates, in that, under dehydration conditions, esterifications may be reversible, whereas boronate formation from borinates is not. In the first, therefore, products may be thermodynamically controlled, whereas kinetic control will operate in the second. It is noteworthy, however, that products obtained from several glycopyranosides (a) by use of an ethylboronate derivative, and (b) by way of the per(diethylbor-inates) had the same structures.338... 

Column separations of the products of hydrolysis of carbohydrate boronates by use of anionic resins provides an alternative, efficient means of deboronation,27,67 69 and other similar separations have used columns of cellulose,48 alumina,67 and, for carbonyl-containing compounds, anion-exchange resins in the hydrogensulfite form.53 In special cases, electrophoresis30 and direct crystallization23 have been employed. 

The chemistry of carbohydrate boronates has been reviewed. Borate has been used as a blocking group which could be selectively removed in the presence of isopropylidene acetals. The method was used to synthesize 6-methacrylates as monomers for polymerization. Chelation of pentitols with boric and germanic... 

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