Iodonium ion assisted synthesis of a common inner core trisaccharide fragment corresponding to the cell-wall phenolic glycolipid of Mycobacterium kansasii
1992; Elsevier BV; Volume: 48; Issue: 46 Linguagem: Inglês
10.1016/s0040-4020(01)89043-8
ISSN1464-5416
AutoresKorien Zegelaar-Jaarsveld, Gijs A. van der Marel, Jacues H. van Boom,
Tópico(s)Mycobacterium research and diagnosis
ResumoThe spacer containing trimer 4-(aminoethyl)phenyl 2,4-di-O-Me-3-O-[2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-α-l-fucopyranosyl)-α-l-rhamnopyranosyl]-α-l- rhamnopyranoside (2) was prepared by stepwise extension of 4-[2-(benzyloxycarbonyl-amino)ethyl]phenyl 2,4-di-O-methyl-α-l-rhamnopyranoside (19) with properly protected ethyl thioglycosides of l-rhamnose 8 and l-fucose 12 or 16 using iodonium ions as promotors. The resulting trimers 22 or 23 were deblocked in two steps to give homogeneous 2. Alternatively, fully protected trimer 22 was assembled by iodonium ion assisted condensation of the phenyl 1-thio-α-l-rhamnopyranoside 29 with 12 followed by extension of dimer 31 with 19.
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