Synthesis of LACTO-N-NEOTETRAOSE (cas 13007-32-4) and lacto-N-tetraose using the dimethylmaleoyl group as amino protective group
-
Add time:08/30/2019 Source:sciencedirect.com
The disaccharide donor O-[2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-α,β-d-glucopyranosyl] trichloroacetimidate (7) was prepared by reacting O-(2,3,4,6-tetra-O-acetyl-α-d-galactopyranosyl) trichloroacetimidate with tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside to give the corresponding disaccharide 5. Deprotection of the anomeric center and then reaction with trichloroacetonitrile afforded 7. Reaction of 7 with 3′-O-unprotected benzyl (2,4,6-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside (8) as acceptor afforded the desired tetrasaccharide benzyl (2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→4)-(3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-d-glucopyranosyl)-(1→3)-(2,4,6-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside. Replacement of the N-dimethylmaleoyl group by the acetyl group, O-debenzylation and finally O-deacetylation gave LACTO-N-NEOTETRAOSE (cas 13007-32-4). Similarly, reaction of O-[(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-α,β-d-glycopyranosyl] trichloroacetimidate as donor with 8 as acceptor afforded the desired tetrasaccharide benzyl (2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→3)-(4,6-benzylidene-2-deoxy-2-dimethylmaleimido-β-d-glucopyranosyl)-(1→3)-(2,4,6-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside. Removal of the benzylidene group, replacement of the N-dimethylmaleoyl group by the acetyl group and then O-acetylation afforded tetrasaccharide intermediate 15, which carries only O-benzyl and O-acetyl protective groups. O-Debenzylation and O-deacetylation gave lacto-N-tetraose (1). Additionally, known tert-butyldimethylsilyl (2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-d-glucopyranoside was transformed into O-[2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→3)-4,6-di-O-acetyl-2-deoxy-2-dimethylmaleimido-α,β-d-glucopyranosyl] trichloroacetimidate as glycosyl donor, to afford with 8 as acceptor the corresponding tetrasaccharide 22, which is transformed into 15, thus giving an alternative approach to 1.
We also recommend Trading Suppliers and Manufacturers of LACTO-N-NEOTETRAOSE (cas 13007-32-4). Pls Click Website Link as below: cas 13007-32-4 suppliers
Prev:Enzymatic supported synthesis of LACTO-N-NEOTETRAOSE (cas 13007-32-4) using dendrimeric polyethylene glycol
Next:Syntheses of a series of LACTO-N-NEOTETRAOSE (cas 13007-32-4) clusters using a carbosilane dendrimer scaffold) - 【Back】【Close 】【Print】【Add to favorite 】
- Related Information
- Pre-clinical safety assessment of the synthetic human milk, nature-identical, oligosaccharide LACTO-N-NEOTETRAOSE (cas 13007-32-4) (LNnT)09/01/2019
- Syntheses of a series of LACTO-N-NEOTETRAOSE (cas 13007-32-4) clusters using a carbosilane dendrimer scaffold08/31/2019
- Enzymatic supported synthesis of LACTO-N-NEOTETRAOSE (cas 13007-32-4) using dendrimeric polyethylene glycol08/29/2019
- The chemical synthesis of human milk oligosaccharides: LACTO-N-NEOTETRAOSE (cas 13007-32-4) (Galβ1→4GlcNAcβ1→3Galβ1→4Glc)08/28/2019