Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Bromopriopionaldehydediethylacetal, is researched, Molecular C7H15BrO2, CAS is 3400-55-3, about Favored formation of an O-glycoside during ribosidation of 5-methyl-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one.Formula: C7H15BrO2.
Condensing (±)-(EtO)2CHMeCHCH(CN)CO2Et and thiourea gave pyrimidine I. Alkylating I at 2-SH group with Me2SO4 followed by ring closure gave pyrrolo[2,3-d] pyrimidine II (R = Me, R1 = H) (III). Silylating III and then treating with 2,3,5-tri-O-acetyl-1-bromo-D-ribofuranose in the presence of Hg(II) salts gave nucleoside IV (R = Ac), not the N-7-glycoside from ribosidation of 2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one. Hydrolysis of IV (R = Ac) under mild conditions gave IV (R = H), which had a UV spectrum similar to II (R = R1 = Me) down to pH 2. At a lower pH hydrolysis of the glycosidic bond occurs.
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Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics