Abstract
AbstractFive carbocyclic analogs of glycosylamides, N‐(5a‐carba‐D‐glycopyranosyl)‐N‐octadecyldodecanamides 2–6, having β‐galacto, α‐ and β‐gluco‐, and α‐ and β‐manno configurations, were synthesized by coupling of the protected anhydro derivatives 12, 15, and 21 of 5a‐carba‐sugars with octadecylamine, followed by N‐acylation. Walden inversion of the 2‐OH functions of 17 and 24 was carried out through O‐sulfonylation. A bioassay (in vivo) of 5a‐carbaglycosylamides showed that they are potent immunomodulators, obviously comparable to the true sugar analogs, suggesting that the 5acarbasugar analogs may provide appropriate model compounds for biochemical studies in glycolipid chemistry. magnified image
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