Saccharide polymers, 3. Synthesis and polymerization of a 5,6-unsaturated fructofuranoid derivative

Wick, Stefan; Yaacoub, Emile-Joseph

doi:10.1002/(sici)1521-3935(20000101)201:1<93::aid-macp93>3.0.co;2-1

Cited by 7 publications

(5 citation statements)

References 12 publications

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“…This example showed that methylene derivatives such as 108 are poor radical acceptors, even when reacted with electrophilic radicals . Unexpectedly, we have been able to show that tributyltin radicals can add to C -methylene sugars .…”

Section: 13 Chain Extension By New Carbon−carbon Bond Formationmentioning

confidence: 57%

Synthesis and Uses of exo-Glycals

2003

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Section: 13 Chain Extension By New Carbon−carbon Bond Formationmentioning

confidence: 57%

Synthesis and Uses of exo-Glycals

2003

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“…The optical rotation of the saccharide copolymers increases with increasing GEL content in the polymer as observed previously. [3,6] The correlation of the polymer composition and the corresponding specific optical rotation for the copolymers with VLa and VSt is shown in Figure 9. The linear regression of the selected range obeys the following equation: [a] D 23 ¼ 0.92 m GEL À 0.196 (correlation coefficient, R 2 ¼ 0.97) for GEL/VLa and [a] D 23 ¼ 1.05 m GEL À 4.16 (R 2 ¼ 0.97) for GEL/VSt (with m GEL ¼ mol-% of GEL in the copolymer).…”

Section: Characterization Of Copolymers Of Gel With Vinyl Estersmentioning

confidence: 99%

“…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.…”

Section: Introductionmentioning

confidence: 99%

Saccharide Polymers 6

Boltres

Schmalbruch

Buchholz

2004

Macro Chemistry & Physics

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Summary: The 2,4,6‐tri‐O‐acetyl‐3‐deoxy‐D‐erythro‐hex‐2‐enono‐1,5‐lactone, briefly Ac‐Gluc‐enlactone (GEL) (1), is easily synthesized in an one‐step reaction from glucono‐δ‐lactone with good yields. Free radical polymerizations of GEL with vinyl esters with side chain of different length including fatty acids esters were carried out in substance or in solution under various conditions. The structures and chemical compositions of the polymers were established by elemental analysis, FT‐IR‐, 1H‐, and 13C NMR spectroscopy. Copolymerization kinetics were investigated. Characteristic properties of polymers, e.g. molecular weight, optical rotation, and thermal properties are reported. The products are of interest as components in commodities with binding and adhesive properties. magnified image

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“…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.…”

Section: Copolymerisation Of 12-exo-fructal Derivatives and Charactementioning

confidence: 99%

“…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.…”

Section: Introductionmentioning

confidence: 99%