Syntheses of a series of LACTO-N-NEOTETRAOSE (cas 13007-32-4) clusters using a carbosilane dendrimer scaffold

Add time:08/31/2019    Source:sciencedirect.com

4-Pentenyl (2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→4)-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-(2,6-di-O-benzoyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-β-d-glucopyranoside (4) was synthesized by regioselective glycosylation of 4-pentenyl (2,6,-di-O-benzoyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-β-d-glucopyranoside and (2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl chloride. By conversion of the protecting groups followed by thioacetylation, 4 was transformed into the corresponding LACTO-N-NEOTETRAOSE (cas 13007-32-4) derivative, 5-(acetylthio)pentenyl (2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→4)-O-(3,6-di-O-acetyl-2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→3)-(2,4,6-di-O-acetyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-β-d-glucopyranoside (6). The lacto-N-neotetraose derivative 6 was introduced into carbosilane dendrimer cores of three shapes, and three kinds of new carbosilane dendrimers peripherally functionalized by lacto-N-neotetraose were obtained.

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