Regioselective (phenylcarbamoyl)ation of polyhydroxy compounds by phenyl isocyanate-Zinc naphthenate (cas 12001-85-3)

Add time:07/20/2019    Source:sciencedirect.com

In the presence of zinc naphthenate as the catalyst, the reaction of phenyl isocyanate with 1,2-propanediol and 3,4-O-isopropylidene-d-mannitol gave the primary phenylcarbamates in high yield. 1,2,6-Hexanetriol was selectively phenylcarbamoylated at O-1, and N6-benzyladenosine at O-2′. The common methyl aldohexo- and aldopento-pyranosides gave the 3-mono(phenylcarbamate)s in fair to excellent yields, along with substantial proportions of the 2-esters in some cases. When the zinc salt was not used, O-6 was the most reactive of the oxygen atoms in the hexopyranosides.

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