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21
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33645786496
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note
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17
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31
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84986701217
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Primeverose was obtained by hydrogenolysis of its benzyl primeveroside, which in turn was isolated by extraction of green fruits of Prunus laurocerasus following the procedure of
-
Primeverose was obtained by hydrogenolysis of its benzyl primeveroside, which in turn was isolated by extraction of green fruits of Prunus laurocerasus following the procedure of. Weinges K., Schick H., Lautenschläger M., and Schilling G. Liebigs Ann. Chem. (1991) 703-705
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0042983198
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For a recent review on aldose→ketose rearrangements see:
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34
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see also Ref. 25
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Chem. Abstr. 9 (1973) 126 744v see also Ref. 25
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927
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33645758180
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note
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31 is based on a β-d-glucose aluminate complex (i), which via a β-d-glucopyranose-1,3-aluminate (ii) and the acyclic 1,3-bridged enediolate intermediate iii proceeds to a 1,3,6-tridentate complex of type iv, that yields fructose on acidification: {A figure is presented}Of the intermediates formulated, ii appears precarious in that the pyranoid ring is forced into a sterically unfavourable boat conformation, and postulation of the sterically demanding tridendate complex iv is not essential since the 6-O-glycosyl-glucose→-fructose conversions 5-7→8-10, in which intermediates of type iv are precluded, proceed with comparative ease and efficiency.
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48
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59
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33645787733
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note
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HPLC indicated aside melibiulose 8 (∼90%) the presence (∼1-2% each) of melibiose 5 of the component sugars galactose, glucose and fructose with traces of higher saccharides.
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60
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33645778470
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note
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The presence of molecular sieve appears essential to bind the water formed during dehydration; otherwise substantial hydrolysis of the glycosyl-HMF's occurs.
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