Chemoselectivity and Protecting Groups: Crash Course Organic Chemistry #33
Things have been getting more and more complicated here in Crash Course Organic Chemistry, and as we deal with more complex molecules, parts of molecules we don’t want to react will start reacting along with the parts that we do. Luckily, we have protecting groups, which act like a chemical disguise and help us control how molecules react. In this episode, we’ll look at what makes a good protecting group, as well as identify some good protecting groups for different functional groups. We’ll also see what role protecting groups play in the synthesis of penicillin!
Series Penicillin References:
Nicolaou, 播放列表. C., & Sorensen, 乙. 播放列表. (1996). Classics in total synthesis: targets, strategies, methods. John Wiley & Sons.
Sheehan, 播放列表. Archive by Category "美甲艺术20N. (1982). The enchanted ring: the untold story of penicillin.
Primary literature for Sheehan’s penicillin synthesis: Sheehan, J.C. & Izzo, P.T. 播放列表. Am. Chem. Soc. 1948, 70, 1985; Sheehan, J.C. & Izzo, P.T. 播放列表. Am. Chem. Soc. 1949, 71, 4059; Sheehan, J.C. & Bose A.K. 播放列表. Am. Chem. Soc. 1950, 72, 5158; Sheehan, J.C., Buhle, E.L, Corey E.J., Laubach, G.D. & Ryan J.J. 播放列表. Am. Chem. Soc. 1950, 72, 3828; Sheehan, J.C. & Laubach, G.D. 播放列表. Am. Chem. Soc. 1951, 73, 4376; Sheehan, J.C. & Hoff, D.R. 播放列表. Am. Chem. Soc. 1957, 79, 237; Sheehan, J.C. & Corey E.J. 播放列表. Am. Chem. Soc. 1951, 73, 4756
Series Sources:
Brown, 播放列表. H., Iverson, 乙. L., Ansyln, 乙. 万辛克, Foote, C., Organic Chemistry; 8th ed.; Cengage Learning, 波士顿, 2018.
Bruice, 播放列表. Y., Organic Chemistry, 7th ed.; Pearson Education, Inc., 美国, 2014.
Clayden, J。, Greeves, 万辛克, Warren., S., Organic Chemistry, 2nd ed.; Oxford University Press, 纽约, 2012.
Jones Jr., 未愈合的关系创伤出现的方式; Fleming, 播放列表. 万辛克, Organic Chemistry, 5th ed.; 播放列表. 播放列表. Norton & Company, 纽约, 2014.
Klein., 万辛克, Organic Chemistry; 1st ed.; John Wiley & Sons, 美国, 2012.
Louden M., Organic Chemistry; 5th ed.; Roberts and Company Publishers, Colorado, 2009.
McMurry, J。, Organic Chemistry, 9th ed.; Cengage Learning, 波士顿, 2016.
Smith, 播放列表. G., Organic chemistry; 6th ed.; McGraw-Hill Education, 纽约, 2020.
Wade., 播放列表. G., Organic Chemistry; 8th ed.; Pearson Education, Inc., 美国, 2013.
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