Lavrenov S N, Solovyeva N P, Reznikova M I, Anisimova O S, Preobrazhenskaya M N
Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russia.
Nucleosides Nucleotides Nucleic Acids. 2004;23(1-2):281-9. doi: 10.1081/ncn-120027835.
The per-O-acetylated open chain derivatives of 1-(1-butylindol-3-yl)-1-deoxy-1-L-sorbose and 1-(1-butylindol-3-yl)-1-deoxy-L-tagatose, which are readily available by alkaline degradation of 1-butylascorbigen followed by acetylation, were used in a nucleoside-type synthesis. The interaction of these ketoses derivatives with bis-(trimethylsilyl)-uracil yielded in each case a mixture of (E)-2,4,5,6-tetra-O-acetyl-1-(1-butylindol-3-yl)-1,3-dideoxy-3-(uracil-1-yl)-L-xylo-hexa-1-enitol and (E)-2,4,5,6-tetra-O-acetyl-1-(1-butylindol-3-yl)-1,3-dideoxy-3-(uracil-1-yl)-L-lyxo-hexa-1-enitol, which were separated by preparative HPLC. The deacetylation of each of these compounds by MeONa in MeOH produced a mixture of 1-(1-butylindol-3-yl)-1,3-dideoxy-4-O-methyl-3-(uracil-1-yl)-alpha-L-sorbopyranose and 1-(1-butylindol-3-yl)-1,3-dideoxy-4-O-methyl-3-(uracil-1-yl)-beta-D-fructopyranose, which were also separated by HPLC, the structures were confirmed by NMR.
1-(1-丁基吲哚-3-基)-1-脱氧-1-L-山梨糖和1-(1-丁基吲哚-3-基)-1-脱氧-L-塔格糖的全-O-乙酰化开链衍生物可通过1-丁基抗坏血酸的碱性降解后乙酰化轻松获得，并用于核苷型合成。这些酮糖衍生物与双-(三甲基甲硅烷基)-尿嘧啶相互作用，每种情况下均产生(E)-2,4,5,6-四-O-乙酰基-1-(1-丁基吲哚-3-基)-1,3-二脱氧-3-(尿嘧啶-1-基)-L-木糖-1-烯醇和(E)-2,4,5,6-四-O-乙酰基-1-(1-丁基吲哚-3-基)-1,3-二脱氧-3-(尿嘧啶-1-基)-L-来苏糖-1-烯醇的混合物，通过制备型高效液相色谱法进行分离。这些化合物中的每一种在甲醇中用甲醇钠进行脱乙酰化，产生1-(1-丁基吲哚-3-基)-1,3-二脱氧-4-O-甲基-3-(尿嘧啶-1-基)-α-L-山梨吡喃糖和1-(1-丁基吲哚-3-基)-1,3-二脱氧-4-O-甲基-3-(尿嘧啶-1-基)-β-D-果糖吡喃糖的混合物，也通过高效液相色谱法进行分离，其结构通过核磁共振光谱法得到确认。
