Peracetylated laminaribiose: preparation by specific degradation of curdlan and its chemical conversion into N-acetylhyalobiuronic acid (cas 13551-21-8)

Add time:08/10/2019    Source:sciencedirect.com

β-Laminaribiose octaacetate (2b) was prepared in greater than 50% yield from the microbial polysaccharide curdlan by specific degradation with a yeast cell-wall lytic enzyme preparation, Kitalase, and subsequent acetylation. Acetolysis of curdlan also gave α-laminaribiose octaacetate (2a) in 27% yield. The usefulness of these peracetates 2a and 2b as starting materials for organic synthesis was shown by converting 2b into N-acetylhyalobiuronic acid (23), the disaccharide repeating unit of hyaluronic acid. The conversion was carried out via series of reactions, which included azidonitration of the glucal derivative and selective alkylidenation or direct tritylation to discriminate two primary hydroxyl groups existing in the disaccharide intermediates.

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