Simple Approach to O-Protected Deaminotunicaminyluracil

Article abstract of DOI:10.1016/S0040-4020(01)87008-3

A five-step synthesis of deaminotunicaminyluracil is presented.Coupling of the ylide, generated from the phosphonium salt 4, with the aldehyde 5 afforded the undecose 6 in high yield.The key step in this synthesis was the hydroboration-oxidation reaction of the olefin 6.For this purpose several hydroborating reagents were examined.The diborane-THF reagent led to the desired deaminotunicamine derivative 8, as the predominant product.Condensation of undecose 8c with 1,3-di-O-trimethylsilyluracil gave the title compound.