1,2,5-ortho esters of D-arabinose as versatile arabinofuranosidic buildingblocks. Concise synthesis of the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis

Authors
Bamhaoud, T Sanchez, S Prandi, J
Citation
T. Bamhaoud et al., 1,2,5-ortho esters of D-arabinose as versatile arabinofuranosidic buildingblocks. Concise synthesis of the tetrasaccharidic cap of the lipoarabinomannan of Mycobacterium tuberculosis, CHEM COMMUN, (8), 2000, pp. 659-660
Citations number
28
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
8
Year of publication
2000
Pages
659 - 660
Database
ISI
SICI code
1359-7345(2000):8<659:1EODAV>2.0.ZU;2-T
Abstract
1,2,5-ortho esters of d-arabinose were found to be ideally suited building blocks for the stereoselective formation of alpha and beta arabinofuranosid ic linkages after nucleophilic opening of the orthoester with oxygen and su lfur nucleophiles; the tetrasaccharidic cap of the lipoarabinomannan of Myc obacterium tuberculosis was then synthesized in a highly convergent manner.