.16 R-bromo Pregnane-3s, 20s-diol Diacetate Fragmentation Reaction Of The Synthesis Of The Steroidal Muscle Relaxants

Tigogenin is a byproduct in the hemp-making industry using the sisal. The industry would normally Tigogenin mixed sisal hemp in the system of industrial wastewater discharged into the water, causing greater pollution. If the Tigogenin can not be a reasonable treatmented and used, it is bound to intensify their effects on human ecological harm to the environment.Based on the research on the rational utilization of steroidal saponins, the direct oxidative degradation of tigogenin into pregnanetriol and 5-methyl tetrahydropyran-2-one by using hydrogen peroxide in a scale of ten kilograms have been achieved in our research group. And then we also found that pregnanetriol can be transformed regioselectively into 16R-bromopregnane-3S,20S-diol diacetate. Its mild reaction conditions, high regioselectivity, and the ability to expand the number of kilograms reaction, simple operation, as much to offer the possibility of industrial production. It is reasonable for our discussion group to further the use of sisal sapogenin resources provide new ideas.As the continuation of previous research, my thesis focused on the exploring of the fragmentation reaction of 16R-bromopregnane-3S,20S-diacetate. We investigated in detail the reaction temperature, pressure, and amount of different alkali, solvent, reaction time, reaction conditions on the fragmentation reaction. Under the condition of t-BuOK/t-BuOH at 100℃,0.25 MPa, we found that androst-16-en-3-ol can be taken in 72% yield.In order to make better use of androst-16-en-3-ol, we tried to apply steroid muscle relaxant pancuronium Synthesis. After multi-step synthesis, we get an important intermediate--3α,17a-biacetyloxy-2β,16β-bipiperidinium-5α-androstane.