On March 31, 1991, Peters, Thomas; Weimar, Thomas published an article.Formula: C16H19NO6S The title of the article was Improved synthesis of α-L-Fuc(1 → 4)-β-D-GlcNAc and α-L-Fuc(1 → 6)-β-D-GlcNAc building blocks: a convergent strategy employing 4-O → 6-O acetyl migration; NOE data on protected α-1,4-linked disaccharides. And the article contained the following:
The synthesis of the two thioethyl disaccharide building blocks I (R1 = PhCH2, R2 = Ac, R3 = phthalimido, R4 = SEt) and II (same R1-R4) was achieved via coupling of fucosyl bromide III with the acceptor alcs. IV (R5 = Ac, R6 = H) and IV (R5 = H, R6 = Ac) under in situ anomerization conditions. The selectively protected 2-deoxy-2-phthalimidoglucose derivative IV (R5 = H, R6 = Ac) was derived from by utilizing an optimized acetyl migration reaction. The thioethyl function in disaccharides I and II was activated with bromine, and excess bromine was removed with cyclohexene. The sensitive 1,6-linkage in the disaccharide I proved to be stable under these activating conditions. The disaccharide bromides I (R1 = CH2Ph, R2 = Ac, R3 = phthalimido, R4 = Br) and II (R1 = CH2Ph, R2 = Ac, R3 = phthalimidi, R4 = Br) were treated with methanol to afford after deblocking the Me glycosides I (R1 = R2 = H, R3 = AcNH, R4 = OMe) and II (R1 = R2 = H, R3 = AcNH, R4 = OMe). Homonuclear 1H-NOE data were obtained for the protected 1,4-linked disaccharide II (R1 = PhCH2, R2 = Ac, R3 = phthalimido, R4 = SEt) suggesting that its preferred solution conformation is rather similar to the solution conformation of the deblocked disaccharide II (R1 = R2 = H, R3 = AcNH, R4 = OMe) in aqueous solution as known from literature data. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Formula: C16H19NO6S
The Article related to fucosyl bromide glycosidation thioglycoside, fucosylglucosamine thioglycoside building block, disaccharide thioglycoside building block, deoxyphthalimidoglucose glycosidation fucosyl bromide, conformation disaccharide glycoside linkage and other aspects.Formula: C16H19NO6S
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles