Synthesis of amphiphilic compounds exposing S-linked beta-N-acetylglucosamine

VICENTE PEÑA GARCÍA; PABLO HÉCTOR DI CHENNA; MARÍA LAURA UHRIG

Tiradentes

Congreso; 18th BRAZILIAN MEETING ON ORGANIC SYNTHESIS; 2022

Previous results obtained in our group showed that L-tartaric acid could be used a convenient scaffold for the access to amphiphilic compounds with good self-assembly properties. Thus, as part of our ongoing project on the development of sugar-containing multivalent ligands by supramolecular approaches, we extended this methodology to incorporate S-linked β-N-acetylglucosamine residues. Starting from the N,N?-dialquinyldiamide 1, we obtained the diacyl derivatives 2 and 3 by treatment with octanoyl and dodecanoyl chloride respectively. On the other hand, derivative 4 was prepared by a one-pot protocol from 1,3,4,6-tetra-O-acetyl- 2-acetamidoglucose with thiourea in the presence of BF3, followed by reaction with 1-azido-2-(2-bromoethoxy)ethane.2 Finally, click reaction of the hydrophobic platforms 2 and 3 with 4 led to the pursued products 5 and 6 in 73% and 77% yields, respectively. Compounds 5 and 6 showed a strong tendency toform self-assembled systems in water. Compound 5 led to a stable hydrogel having a Tg = 52ºC.