New type of alfa-tocopheryl glycoconjugate containing 5-carbon linker was described. The alfa-tocopherylallyl ether was combined to peracetylated 3-butenyl alfa-manno pyranoside by cross metathesis. Transformation of the linker to easier cleavable enol ether was attempted.
Selective bromination of alfa-tocopherol acetate with bromine in the presence of HgO (Br2O in situ) to 5-bromomethyl-gama-tocopherol acetate was carried out. Bromination of alfa-tocopherol acetate with NBS led to 3,4-dehydro-alfa-tocopherol acetate. No basic catalyst for dehydrobromination of intermediate 4-bromo derivative was needed.
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