jo026325a_si_001.pdf (624.05 kB)

A One-Pot Strategy for Synthesis of 5-O-(α-d-Arabinofuranosyl)-6-O-(β-d- galactofuranosyl)-d-galactofuranose Present in Motif E of the Mycobacterium tuberculosis Cell Wall

Download (624.05 kB)
journal contribution
posted on 14.02.2003, 00:00 by Hairong Wang, Jun Ning
5-O-(α-d-Arabinofuranosyl)-6-O-(β-d-galactofuranosyl)-d-galactofuranose 6 present in motif E of the Macobacterium tuberculosis cell wall has been regio- and stereospecifically synthesized using 3-O-benzoyl-1,2-O-isopropylidine-α-d-galactofuranose (10) as the glycosyl acceptor by the trichloroacetamidate method in a one-pot manner. The diol glycosyl acceptor 10 was smoothly derived from 1,2:5,6-di-O-isopropylidene-α-d-galactofuranose (8) by 3-O-benzoylation and then selective 5,6-O-deacetonation. The preparation of 8 was greatly improved by increasing the ratio of DMF to acetone and using a solid-supported catalyst.