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preparation of C20- lipid II analogs (experiment (nerol to 1 (Nerol() was…

- - - - TLC/rf
- - - - Since we added TBDPSCl to nerol as a protecting group, it would conduct undesired deprotection in the presence of strong acid. If we did not track the reaction carefully, the yield of the compound 3 would drop dramatically.
    - - From the process of 3 to 4, we chose to add methanol as solvent before. However, NaBH4 would react with methanol first and reduce its ability of reduction. Therefore, we had to add more equivalence of NaBH4 to the reaction mixture. But, if we replaced methanol with ethanol, the reaction would be mild between NaBH4 and solvent, which could decrease the consumption of NaBH4.
    - - From the process of 4A to 4B, we got dull red solution. However, it should not be this color theoretically. We supposed that some side reactions happened because we left it to react for overnight. To remove the side products, we purified the mixture by column chromatography to obtain compound 4B as colorless oil.
    - - To obtain compound 5, we added ether to make product precipitate and then filtered. If the product were not white enough, we would add acetone to dissolve it, followed by addind ether again to enhance its purity.
    - - In scheme 1, we wanted to prepare polyprenoid alcohols with chloride as a leaving group.
- - - - Thanks for Chi-Hua Wu. From the theory to the synthesis skills, she helped me to establish the right concepts and attitude. Sometimes, due to lack of enough experience, I made some troubles for her. Instead of blaming on me, she always patiently told me how to handle these situations if I encountered alone next time.
      - Furthermore, I appreciated for Wei-Chieh Cheng teacher to give me the opportunity to learn in this laboratory. I could conduct experiment with sufficient source and equipments, which really made me improve a lot in the synthesis field.