Synthesis of 6-0-(α-D-mannopyranosyl)-D-myo-inositol: a fragment from mycobacteria phospholipids
1990; Elsevier BV; Volume: 46; Issue: 24 Linguagem: Inglês
10.1016/s0040-4020(01)81480-0
ISSN1464-5416
AutoresC. J. J. Elie, R. Verduyn, C. E. DREEF, D. M. Brounts, G. A. VAN DER MAREL, J. H. VAN BOOM,
Tópico(s)Polyamine Metabolism and Applications
ResumoCondensation of 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride (12) or ethyl 2-O- benzoyl-3,4,6-tri-0-benzyl-1-thio-α-D-mannopyranoside (13) with racemic 1,2-0-cyclohexylidene-3,4,5 tri-O-benzyl- myo-inositol (11) gave, after deacylation and column chromatography, the enantiomorphs 16a and 16b. Benzylation, acid hydrolysis of the 1,2-O-cyclohexylidene group and regioselective allylation of 16b led to 4b, which was deblocked by deallylation and hydrogenolysis to give 6-O-(α-O-D-mannopyranosyl)-D-myo-inositol (5b). Any attempt to glycosylate the hydroxyl at the axial C-2 position of the myo-inositol moiety in 4b with the mannopyranosyl fluoride 12 or the ethyl thiomannopyranoside 13 failed.
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