Portal de Periódicos da CAPES

Synthesis of 2-acetamido-6-O-(5-acetamido-3,5-dideoxy-β-d-glycero-d-galacto-2-nonulopyranosylonic acid)-2-deoxy-d-glucose [2-acetamido-6-O-(N-acetyl-β-d-neuraminyl)-2-deoxy-d-glucose]

1982; Elsevier BV; Volume: 105; Issue: 1 Linguagem: Inglês

10.1016/s0008-6215(00)81851-0

1873-426X

Dominicus J.M. van der Vleugel, Jan W. Zwikker, Johannes F.G. Vliegenthart, S. A. A. VAN BOECKEL, Jacques H. van Boom,

Chemical Synthesis and Analysis

Silver triflate-promoted condensation of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-β-d-glycero-d-galacto -2-nonulopyranosonate (9) with benzyl-2-acetamido-2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-d-glucopyranoside, followed by removal of the 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl group and subsequent acetylation, afforded a 4:1 mixture of benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-d-glycero-d-galacto-2-nonulopyranosylonate)-α-d-glucopyranoside (13) and the (2→6)-α-linked isomer. After selective crystallisation, 13 was obtained in 46% yield based on the precursor of 9, methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-d-glycero-d-galacto-2-nonulopyranosonate (8). An additional product of the condensation reaction was methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-d-glycero-d-galacto-non-2-enopyranosonate, which was obtained in 40% yield based on 8. O-Deacetylation of 13 and subsequent saponification gave benzyl 2-acetamido-2-deoxy-6-O-(potassium 5-acetamido-3,5-dideoxy-β-d-glycero-d-galacto-2-nonulopyranosylonate)-α-d-glucopyranosi de (16). Catalytic hydrogenolysis of 16 yielded the title product as its potassium salt.