Abstract
The concept of double stereodifferentiation in Sharpless asymmetric
dihydroxylation has been studied and the results obtained are applied
to the diastereoselective syntheses of xylo -isomers
of C18 -phytosphingosine. The diastereomeric mixture obtained
could be separated by column chromatography. Thus, the l -xylo -(2R ,3S ,4S )-C18 - and d -xylo -(2S ,3R ,4R )-C18 -phytosphingosines
as their tetraacetate derivatives were synthesized in diastereomerically
pure form.
Key words
dihydroxylation - diastereoselectivity - stereoselective synthesis - sphingolipids - amino alcohols
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