Alditols properties

V. Table of Properties of 2,5-Anhydrides of Sugars, Alditols, and Aldonic Acids... 

Tables VI-XI show the physical properties of the alditol anhydrides and certain of their derivatives.

In view of this, a new overview of developments in this area is warranted, especially as no special summary on this subject has been published for some time. A comprehensive article2 in a previous volume of this series appeared in 1950. Subsequently, a brief discussion of 1,4 3,6-dianhydrohexitols was incorporated in a contribution on the stereochemistry of cyclic derivatives of carbohydrates,3 and they were treated exhaustively within a summary of alditol anhydrides that contained tables of physical properties of derivatives.4... 

Peracetylated derivatives of alditols and reduced sugars are sufficiently stable for GC analysis and possessing good properties, but a relatively complicated procedure is required for their preparation. They also cannot be applied to the simultaneous determination of the sugar and the corresponding alditol with xylose, 2- and 4-substituted isomers cannot be resolved owing to the symmetry of xylitol. This gave rise to the use of combination with other derivatives, firstly with nitriles [442]. The procedure for a standard mixture... 

All monosaccharides and their derivatives that possess aldehyde or ketone groups (that is, excepting derivatives such as alditols and aldonic acids) will have reducing properties. Moreover, those with the appropriate number of carbon atoms can form rings occurring in two forms (anomers) and in which the potential reducing carbon is called the anomeric carbon. 

The following Tables record some physical properties of boronates of sugars, glycosides, C- and N-glycosyl compounds including nucleosides, alditols, and anhydro sugars. 

Tostevin, J. E., "The Hydrodynamic Properties of the Alditol Oligosaccharides," Ph.D. Dissertation, The Institute of Paper Chemistry, 1966. 

Some empirical rules were devised to correlate the configuration at Cl of the alditolyl chains (C2 of the parent sugar) of 2-(alditol-l-yl)benzimida-zoles with their polarimetric (42JA1612) and spectropolarimetric properties (67JA4129). The mass spectra of these compounds have been investigated (82MI8). 

A new family of linear polyurethanes and poly(ester-urethanes), prepared from both aliphatic and aromatic diisocyanates and isorbide [21] or conveniently protected sugar alditols, has recently been reported and the properties of... 

Complementary to their studies on the 0-nitrobenzylidene acetals of alditols, Tanasescu and coworkers prepared some corresponding derivatives of aldoses and examined their properties on irradiation with ultraviolet light. They found that the di-0-(o-nitrobenzylidene)aldoses are converted into 1,2-0-(o-nitrobenzylidene)-3-0-nitrosobenzoyl derivatives. In a later paper, the formation of optically inactive products from this treatment was described, but the structure of these compounds needs elaborating. These phenomena may be of greater value in effecting transformations in the carbohydrate series when more is known about them. 

Alditols polyols are readily renewable, inexpensive and harmless to the environment. By incorporation of polyols into aliphatic polyesters, functional linear or hyperbranched polymers can be prepared with specific biological activities and/or that respond to environmental stimuli. Polyesters with carbohydrate or polyol repeat units in chains have been prepared by chemical methods. " In some cases, the reaction conditions led to hyperbranched polymers (HBPs). The highly branched architecture of HBPs leads to unusual mechanical, rheological and compatibility properties. " These distinguishing characteristics have garnered interest for their use in numerous industrial and biomedical fields. Chemical routes to linear polyol-polyesters require elaborate protection-deprotection steps ". Furthermore, condensation routes to hyperbranched polymers generally require harsh reaction conditions such as temperatures above 150 C and highly acidic catalysts ". ... 

In order to avoid the formation of anomeric mixtures of derivatives, reducing sugars can be converted into alditols. If mixtures of sugars are analyzed by m.s. in combination with g.l.c., reduction of the sugars to alditols simplifies the separation. However, caution must be exercised, as two different aldoses may give the same alditol owing to symmetry properties. Every ketose affords two alditols on reduction. 

Isomeric glucosylated amino-alditol derivatives, 17, derived from reaction of 2-amino-2-deoxy-mannit-6-yl and -glucit-6-yl a-D-glucopyranosides with methyl methacrylate, were co-polymerized and the physical properties of the resulting polymers were examined in water. 

A preparation of l,5-dideoxy-l,S-imino-D-allitol from A protected deoxynqjirimycin v ch involves a microbial redox reaction at C-3 has been described, and the glycosidase inhibitory properties of the product were determined together with those of other imino-alditols isolated from the leaves of Mens alba (see also ref 40 above). ... 

Alditols, particularly glycerol (I), ethylene glycol, sorbitol, and D-manni-tol, have widespread commercial applications, frequently as a result of their hygroscopic properties. The organic monoesters, particularly of long-chain fatty acids, may have surface-active properties which make them of interest as emulsifiers, but the usual conditions of commercial esterification produce anhydro derivatives simultaneously (Chapter VII). Nitrate esters are important as explosives and as pharmaceuticals. The acetal derivatives (Chapter IV) have been extensively prepared and studied, but as yet have found no practical application. 

A review has been published on the relationship of the conformation of alditols to properties such as chromatographic affinity,... 

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