Question 6: Early results show that remdesivir, an antiviral drug originally developed by Gilead Sciences to treat Ebola, may be a promising...
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I need help with this organic chemistry 2 question, please.

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Question 6: Scientists around the world are conducting more than 300 clinical trials to investigate treatments to help patients infected with the novel coronavirus. Early results show that remdesivir, an antiviral drug originally developed by Gilead Sciences to treat Ebola, may be a promising treatment for COVID-19. Consider the structure of remdesivir: NH HN HO OH remdesivir a) One of the steps in the synthesis of remdesivir involves the protection of a primary amine prior to the formation of an organolithium reagent, which acts as a carbanion in a subsequent synthetic step. The reagent used to protect the primary amine is trimethylsilyl chloride (TMS-CI), as shown below: NH2 TMS TMS 1. 2 TMS-CI, THE TMS-CI: 2. 4 n-BuLi -Si-CI B Draw a multistep arrow-pushing mechanism to show how the primary amine is protected using TMS-CI. Assume that the CI leaving group acts as the base. (5 points) b) In the next step of the reaction sequence, a reaction with a lactone results in the formation of a following tricyclic product. Note that the TMS protecting group is removed using acid after the coupling reaction is complete. TMS Bno -TMS NH- Bno OBn 2. Hot Bno Bno OBn Based on the above reaction, what competing reaction could have occurred if the primary amine was not protected using TMS-CI? (2 points) c) When designing a synthetic scheme, what is more advantageous to try to include: a chemoselective reaction or a protecting group strategy? Explain your reasoning. (2 points)

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