Iodonium ion-assisted synthesis of tetrameric fragments corresponding to the cell wall phenolic glycolipids of Mycobacterium kansasii serovars II and IV

Article abstract of DOI:10.1016/0040-4020(96)00034-8

The spacer-containing tetramers 3 and 4, derivatives of the phenolic glycolipids of Mycobacterium kansasii serovars II and IV were prepared by iodonium ion-mediated mannosylation of trimeric acceptor 4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-[4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-2-O-methyl- α-L-fucopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside (2) with ethyl 1-thio-D-mannopyranoside donors 7, 13 and 24. In addition, the glycosylating properties of donors 7, 13, 24, 29-31, each containing a different protective group at position 2, were examined by executing condensations with model acceptor 18(L) and its enantiomer 18(D).