Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideOn March 31, 1991, Peters, Thomas; Weimar, Thomas published an article in Liebigs Annalen der Chemie. 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》. The article mentions 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. In the experiment, the researchers used Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside)
Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.
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