Synthesis of Polymerizable Hexose Derivatives

✍ Scribed by Koßmehl, Gerhard ;Volkheimer, Jürgen

• Publisher: John Wiley and Sons
• Year: 1989
• Tongue: English
• Weight: 487 KB
• Volume: 1989
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198919890280

✦ Synopsis

Carbohydrates / Hexose derivatives, polymerizable / Hydrogels We are studying hydrogels (crosslinked polymers with a defined water content) from highly hydrophilic monomers. This paper describes the synthesis of acryloyl and methacryloyl hexose derivatives as starting materials for the synthesis of hydrogels. 2,3;4,6-Di-O-isopropylidene-l-~-methacryloyl-a-~~-( -)-sorbofuranose (1 a) was synthesized by two methods from 2,3;4,6-di-Oisopropylidene-a-L-( -)-sorbofuranose (1) and methacryloyl chloride and methacrylic anhydride, respectively. l a was obtained as a syrup, free of inhibitor. Crystalline I-O-acryloyl-2,3;4,6-di-O-isopropylidene-a-L-( -)-sorbofuranose (1 b) was prepared from 1 and acryloyl chloride. D-( -)-Fructose and acetone were condensed according to the method of Van Grunenberg et al.'). This method affords a mixture of isomers consisting of 2,3;4,5-di-O-isopropylidene-P-~-( -)-fructopyranose (2) and 1,2;4,5-di-O-isopropylidene-P-~-( -)-fructopyranose (3) (cf. ref.*)). In 'H-NMR spectroscopy (250 MHz, [D& DMSO), integration of the signals of the alcoholic protons of 2 (6 = 5.04, t) and 3 (6 = 5.22, d) revealed the components 2 and 3 in the ratio 9: 1. This finding was confirmed by GC analysis. The byproduct 3 was removed by acid hydrolysis. c / , O HC HiC' ' CH:

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