端基含甲基保护羧基的三半乳糖苷的设计和合成

Design and synthesis of tris(1-thiogalactopyranoside) having a methyl-protected carboxy group at the aglycon terminals

目的合成端基含羧基衍生功能基的三半乳糖苷。方法以季戊四醇为起始原料,经加成、醇解、还原、磺酰化,再与已知的2-S-(2,3,4,6)-四-O-乙酰基-β-D-半乳吡喃糖基-2-异硫脲氢溴酸盐作用,共5步反应,制得三(ω-2,3,4,6-四-O-乙酰基-β-D-半乳吡喃糖硫基丙氧甲基)(ω-甲氧甲酰乙氧甲基)甲烷。结果和结论合成制得目标化合物,并经1HNMR,IR和MS确证结构。

OBJECTIVE To synthesize Tris- 1 - thiogalactopyranoside having a methyl- protected carboxy group at the aglyeon terminals. METHODS Starting from quaternary pentanetetraol, followed by addition, alcoholysis, reduction, stdfonation and final straightforward condensation with the available versatile saccharide reagent,2 - S - （2,3,4,6） - tetra-O- acetyl- β - D - galactopyranosyl - 2 - thiopseudourea hydrobromide, the title compound tris （ ω - 2,3,4,6 - tetra - O - acetyl - β - D - galactopyranosylthiopropoxymethyl） （ ω - methoxycarbonylethoxymethyl）methane has been synthesized via 5 designed reaction steps.RESULTS and CONCLUSION The title compound was synthesized and confirmed by ^1H- NMR,IR,and MS. Key words： Hepatic targeting; riffs（ ω - 2, 3,4,6 - tetra - O- acetyl - β - D - galactopyranosylthiopropoxymethyl） （ω - methoxy - carbonylethoxymethyl） methane; Synthesis