Synthesis of Higher Sugars via Allytin Derivatives of Simple Monosaccharides

Article abstract of DOI:10.1021/jo00278a001

The addition of monosaccharide allytin derivatives to aldehydo sugars has been examined.The efficiency, rate yield, and stereoselectivity of the reactions are strongly dependent on the Lewis acid catalyst used.The major product is syn, and in the most striking case, two monosaccharides have been coupled directly to give an assembly containing nine contiguous chiral centers.