IODONIUM ION-ASSISTED SYNTHESIS OF TETRAMERIC FRAGMENTS CORRESPONDINGTO THE CELL-WALL PHENOLIC GLYCOLIPIDS OF MYCOBACTERIUM-KANSASII SEROVAR-II AND SEROVAR-IV
K. Zegelaarjaarsveld et al., IODONIUM ION-ASSISTED SYNTHESIS OF TETRAMERIC FRAGMENTS CORRESPONDINGTO THE CELL-WALL PHENOLIC GLYCOLIPIDS OF MYCOBACTERIUM-KANSASII SEROVAR-II AND SEROVAR-IV, Tetrahedron, 52(10), 1996, pp. 3575-3592
The spacer-containing tetramers 3 and 4, derivatives of the phenolic g
lycolipids of Mycobacterium kansasii serovars II and IV were prepared
by iodonium ion-mediated mannosylation of trimeric acceptor 4-[2-(benz
yloxycarbonylamino)ethyl]phenyl -alpha-L-rhamnopyranosyl]-alpha-L-rham
nopyranoside (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).