ISSN:
1022-1352
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The syntheses of new types of vinyl sugars are described whose vinyl groups are connected with the monosaccharide by a C—C bond. Such monomers can be polymerized by radical as well as by anionic initiation. Starting from D-mannitol, D-gluconolactone, D-galactose, and D-fructose, the isopropylidene-protected aldehydes (R)-2,3-isopropylidene-D-glyceraldehyde (3), 2,3;4,5-di-O-isopropylidene-aldehydo-D-arabinose (4), 1,2;3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose (5), and 2,3;4,5-di-O-isopropylidene-β-D-arabino-hexosulo-2,6-pyranose (6) were prepared. Grignard reaction of the aldehyde compounds with 4-vinylphenylmagnesium chloride in tetrahydrofuran (THF) yielded the new styryl monomers of type 1, in each case as a mixture of two diastereoisomers. The corresponding reaction with vinylmagnesium bromide furnished a mixture of two diastereoisomeric allyl alcohol derivatives. Subsequent Swern oxidation (DMSO/(COCl)2) gave the vinyl ketones of type 2. A scale-up procedure (20 L flask) allowed eight different monomers to be prepared on a 50-200 g scale. Furthermore, the synthesis of the 2,3;4,5-di-O-isopropylidene-β-D-fructopyranose could be considerably improved.
Additional Material:
7 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/macp.1996.021970409
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