Add time:08/23/2019         Source:sciencedirect.com

An octasaccharide, β-d-Galp-(1 → 6)-[α-l-Araf-(1 → 2)]-β-d-Galp-(1 → 6)-β-d-Galp-(1 → 6)-[α-l-Araf-(1 → 5)-α-l-Araf-(1 → 2)]-β-d-Galp-(1 → 6)-β-d-Galp-1 → OMP was synthesized. 4-Methoxyphenyl 2,3,4-tri-O-benzoyl-β-d-galactopyranoside (5), 2,6-di-O-acetyl-3,4-di-O-benzoyl-α-d-galactopyranosyl trichloroacetimidate (9), and 4-methoxyphenyl 2-O-acetyl-3,4-di-O-benzoyl-β-d-galactopyranoside (11), 2,3,4,6-tetra-O-benzoyl-α-d-galactopyranosyl trichloroacetimidate (12), and 2,3,5-tri-O-benzoyl-α-l-arabinofuranosyl trichloroacetimidate (17) were used as the synthons. A concise route was used to gain the tetrasaccharide donor 19 by the use of 11, 12, 5, and 17. Meanwhile, treatment of 5 with 9 yielded β-(1 → 6)-linked disaccharide 20, and subsequent selective 6-O-deacetylation produced the disaccharide acceptor 21. Reaction of 21 with 19 gave 22, and subsequent selective 2-O-deacetylation afforded the hexasaccharide acceptor 23. Condensation of 23 with α-l-(1 → 5)-linked arabinofuranose disaccharide 24, followed by deprotection, yielded the target octasaccharide.

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