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Several papers have appeared on the synthesis and reactions of glycoside epoxides synthesised from racemic dihydropyrans. CO,H Scheme 6 4-deoxy-3-O-methyl-c,~-~~-threo-pentopyranoside in good yield showing that such epoxides open preferentially by attack at C-3. A similar finding was obtained during ring-opening with lithium aluminium h ~ d r i d e . l ~ ~ Double resonance experiments have shown that in a series of 3,4-epoxy2-alkoxytetrahydropyrans the epoxide-ring proton nearer the anomeric centre resonates at higher fields than the other.

Nuhn, W. Bley, and G. Wagner, Arch. , 1967, 300, 926. 29 Glycosides acetates. Similarly, 1 -thioglucose gave a water-soluble high molecularweight adduct with fumaric acid, butane-1,3-diol polyester showing strong surface-active properties ,IQ1 A few simple derivatives of ethyl 1-thio-/%D-glucopyranosidehave been reported; these are the 4,6-O-benzylidene derivative and its diacetate and dibenzoate, and ethyl 2,3-di-0-benzoyl- 1 -thio-/3-~-glucopyranoside. 142 C-Glycosides The isolation of a series of C-D-glucosyl and C-D-xylosyl flavones from citrus fruits has been described (including new compounds).

Org. , Alcad. Nauk Kirg. , 1967, 19. lo( J. P. Horwitz, C. V. Easwaran, and L. S. Kowalczyk, J. Org. , 1968, 33, 3174. lo5 M. D. Saunders and T. E. , 1968,6, 121. lo6 D. Piszkiewicz and T. C. Bruice, J. Amer. Chem. , 1968, 90, 5844. lo' D. Piszkiewicz and T. C. Bruice, J. Amer. Chem. ,1968, 90, 2156. l o 3 V. 23 Glycosides that of the ethyl glucoside it was much greater than that of methyl 2-amino2-deoxy-p-~-glucopyranoside. 0 a 4 3 CH,OH HO H -- N C-Me N=C-Me - 9’”” NHAc Scheme 4 Several papers have appeared on the stabilities of glycosidic bonds as parts of investigation into the effects influencing the hydrolyses of glycosidic bonds of polysaccharides.

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