147649-92-1

Upstream product

• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 7464-56-4 1-O-allyl-α-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 

Downstream Products

• 147577-45-5 allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside 
• 147577-18-2 methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate 
• 147577-17-1 allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Total Synthesis of a Chimeric Glycolipid Bearing the Partially Acetylated Backbone of Sponge-Derived Agminoside e

We describe the total synthesis of a chimeric glycolipid bearing both the partially acetylated backbone of sponge-derived agminoside E and the (R)-3-hydroxydecanoic acid chain of bacterial rhamnolipids. The branched pentaglucolipid skeleton was achieved using a [3 + 2] disconnection approach. The β-(1 → 2) and β-(1 → 4)-glycosidic bonds were synthesized through a combination of NIS/Yb(OTf)3- and TMSOTf-mediated stereoselective glycosylations of thiotolyl, N-phenyltrifluoroacetimidate, and trichloroacetimidate donors. Late-stage pentaacetylation, Staudinger reduction of a (2-azidomethyl)benzoyl group, followed by continuous-flow microfluidic hydrogenolysis completed the total synthesis of the structurally simplified glycolipid, whose partial acetylation pattern on the glycan part was identical to agminoside E. Our study lays the foundation for the total synthesis of sponge-derived agminosides and the understanding of their biological functions in sponges.

Chemical Synthesis of Modified Hyaluronic Acid Disaccharides

Herein we report a chemical synthesis towards new modified hyaluronic acid oligomers by using only commercially available d-glucose and d-glucosamine hydrochloride. The various protected hyaluronic acid disaccharides were synthesized bearing new functional groups at C-6 of the β-d-glucuronic acid moiety with a view to structure-related biological activity tests. The orthogonal protecting group pattern allows ready access to the corresponding higher oligomers. Also, 1H NMR studies of the new derivatives demonstrated the effect of the various functional groups on the intramolecular electronic environment.