ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Total synthesis of α-disaccharidyl-2,5,6-trideoxy-streptamines related to aminoglycoside antibiotics derived from maltose and lactoseThe synthesis of the hitherto unknown 4-O-substituted α-linked pseudo-tri-saccharides 1,2 and 3 is described. The key intermediates required in the reaction sequence are the glycals 12, 13 and 14, prepared from maltose, lactose and the chiral ditosyloxy-cyclohexanol 15, readily accessible from quinic acid. The pivotal step in the reaction's scheme - a stereospecific α-glycosylution procedure -, is an acid-catalyzed addition of the alcohol 15 to the glycals 12, 13 and 14 leading to the corresponding 2,3-unsaturated trisaccharides. The latter compounds were transformed to the target α-glycosides of 2,5,6-trideoxystreptamine 1, 2 and 3 which were devoid of significant antibacterial activity. These results indicate that the presence of an ether linkage at the position 4′ is probably critical for antibacterial activity.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19820650536
