Saccharide polymers, 2. Synthesis and polymerization of exo‐glucal derivatives

Abstract

Unsaturated glucopyranose derivatives such as 1,2,3,4-tetra-O-acetyl-6-desoxy-P-~-xylo-hex-5-enopyranose (3) and 1,2,3,4-tetra-O-benzoyl-6-desoxy-~-~-xylo-hex-5-enopyranose (6), briefly called "Ac-exo-glucal (3)" and "Bz-exo-glucal (6)", were synthesized. These exo-cyclic sugar vinyl ethers were investigated in polymerization reactions. The corresponding "saccharide polymers", homo-and copolymers, were synthesized under free radical conditions. The structures and the compositions of the soluble "saccharide polymers" were established by elemental analysis, 'H and I3C NMR, and FT-IR spectroscopy. Characterization of the polymers, like molecular weights and optical rotations are reported. Saccharide polymers with different sugar content and low as well as high molecular weights were obtained.

Saccharide polymers, 4. Synthesis and polymerisation of 1,2-unsaturated fructopyranoid derivatives

“…This result of polymer composition was observed in all polymerisation reactions, independently of monomer composition in feed, the type of monosaccharide (glucose, ribose), its structure (furanoid, pyranoid), the nature of the monosaccharide protecting group, and reaction temperature. [17][18][19] MAh does not homopolymerise under these radical conditions. Therefore, an alternating tendency of this radical copolymerisation can be assumed.…”

“…A variety of "unsaturated monosaccharides", in which the double bond is in the exo-or endo-cyclic position of the pyranoid or furanoid structure of the monosaccharide, have been successfully investigated in free radical polymerisation with a wide range of commercial available comonomers. [17][18][19] These novel polymer materials, called "saccharide polymers" are expected to exhibit specific properties, such as biocompatibility, especially in the field of pharmaceutical, medicine, and cosmetics.…”

Saccharide Polymers, 5

“…We succeeded in the synthesis of such saccharide polymers, as they are termed, early in the nineties. [15][16][17][18][19][20][21] A variety of polymerizable saccharide monomers have been synthesized from sources like glucose, fructose etc. and have been shown to undergo radical copolymerization with a wide range of commercial comonomers.…”

“…and have been shown to undergo radical copolymerization with a wide range of commercial comonomers. [13][14][15][16][17][18][19][20][21] An ongoing problem was to find an easy, convenient way of synthesis of saccharide monomers, which is essential for scale up and utilization.…”

Saccharide Polymers 6

“…These saccharide monomers had pyranoid or furanoid structure with the polymerizable double bond in exo-or endocyclic position. [1][2][3][4][5] Unfortunately, many of the unsaturated derivatives require several steps of synthesis with low yields, which make them less attractive for industry. A challenging task was to find an easy way of synthesis with the possibility of straight scale-up to the preparative and technical scale.…”