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Synlett 1998; 1998(2): 171-173
DOI: 10.1055/s-1998-3127
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Oligosaccharide Synthesis on Controlled-Pore Glass as Solid Phase Material

Alexander Heckel* , Elmar Mross, Karl-Heinz Jung, Jörg Rademann, Richard R. Schmidt
  • *Fakultät Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany; Fax +49/75 31/88 31 35
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Publikationsdatum:
31. Dezember 2000 (online)

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Mercaptopropyl-functionalized controlled-pore glass (MP-CPG, 2) was employed as a solid phase material for the synthesis of α(1-2)-connected trimannoside 16. As a glycosyl donor O-(3,4,6-tri-O-benzyl-2-O-phenoxyacetyl-α-d-mannopyranosyl)trichloroacetimidate (6) was employed which was readily obtained from d-mannose. Glycosylation of 2 and of intermediates 9 and 13 was performed with excess 6 in CH2Cl2 at -40 °C in the presence of TMSOTf as the catalyst (→ 7, 11, 15). For the removal of the temporary phenoxyacetyl (PA) protective group guanidine in DMF was used (→ 9, 13). Cleavage of products 7, 9, 11, 13 and 15 from MP-CPG was carried out with N-bromosuccinimide (NBS) in THF/MeOH in the presence of 2,6-di-tert-butylpyridine (DTBP) affording 8, 10, 12, 14, and methyl trimannoside 16, respectively.

controlled-pore-glass - mercapto functionalized - glycosylation - O-glycosyl trichloroacetimidates - solid phase synthesis - trimannoside, α(1-2)-connected