The structure-activity relationship of lipophilic aza-C-glycosides as inhibitors of the three enzymes of glucosylceramide metabolism is investigated. A library of β-aza-C-glycosides was synthesized with variations in N-alkylation and the linker length/type to the lipophilic moiety. A cross-metathesis reaction was used to prepare a second library of α-aza-Cglycosides with D-gluco, L-ido and D-xylo iminosugar cores

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A one-pot procedure for the preparation of phosphoramidates, phosphorothioates, pyrophosphates, phosphodiesters, and phosphofluoridates has been devised using di(p-methoxybenzyl)-N,N-diisopropylphosphoramidite as the common phosphitylating reagent.

A new conformationally locked aminomethyl C-glycoside has been synthesized and incorporated into oligonucleotides (ONs). The applicability of the monomer in post-ON synthesis (i.e., conjugation by organic synthesis performed on ONs attached to resin) has been successfully demonstrated by condensation with pyren-1-ylcarboxylic acid. The abilities of the pyrenyl-derivatized ONs to recognize abasic sites in complementary strands were investigated by thermal denatur-

[reaction: see text] The natural product pachastrissamine, an anhydrophytosphingosine derivative isolated from various sponges and endowed with cytotoxic activity against several human carcinoma cell lines, was synthesized in three steps and with 72% overall yield from d-ribo-phytosphingosine.