Understanding Protecting Groups in Organic Synthesis: When to Use TBDMS-Cl

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SUMMARY

This discussion focuses on the use of TBDMS-Cl as a protecting group in organic synthesis. Protecting groups are essential for preventing certain functional groups, such as alcohols, from undergoing unwanted reactions during synthesis. The immediate sign to use TBDMS-Cl is the presence of an alcohol that needs to be preserved while reducing a nearby carbonyl. The conversation emphasizes the importance of identifying the functional group to protect and selecting the appropriate reagent for effective synthesis.

PREREQUISITES
  • Understanding of organic functional groups and their reactions
  • Familiarity with protecting group strategies in organic synthesis
  • Knowledge of TBDMS-Cl and its chemical properties
  • Ability to interpret reaction mechanisms and arrow pushing
NEXT STEPS
  • Research the mechanism of TBDMS-Cl in protecting alcohols
  • Explore alternative protecting groups for various functional groups
  • Study the reactivity of protecting groups during reduction reactions
  • Learn about the role of protecting groups in multi-step organic synthesis
USEFUL FOR

Organic chemists, students in chemistry programs, and researchers involved in synthetic organic chemistry will benefit from this discussion, particularly those focusing on reaction mechanisms and protecting group strategies.

member 392791
Hello,

I am unsure of how to utilize protecting groups in organic synthesis problems. What would be an immediate sign to the trained eye that one should use a protecting group such as TBDMS-Cl?
 
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What is the purpose of protecting groups (PG)?
 
To protect something from being reduced completely
 
Look for an alcohol that you want to keep in addition to a carbonyl that you want to reduce
 
Woopydalan said:
To protect something from being reduced completely

  • Draw the reagents you can use for protecting different functional groups.
  • Notice the similar structures between different reagents used to protect a single functional group.
  • Identify the something (functional group) you want to protect.
  • Select a reagent you have available for protecting that functional group.
  • Push arrows.

Here is wiki's list of functional groups and their protecting groups:
http://en.wikipedia.org/wiki/Protecting_group

When I see TBDMS-Cl, I see a radical Cl anion waiting to react with an acidic hydrogen,usually in a hydroxyl group.
 
I came.across a headline and read some of the article, so I was curious. Scientists discover that gold is a 'reactive metal' by accidentally creating a new material in the lab https://www.earth.com/news/discovery-that-gold-is-reactive-metal-by-creating-gold-hydride-in-lab-experiment/ From SLAC - A SLAC team unexpectedly formed gold hydride in an experiment that could pave the way for studying materials under extreme conditions like those found inside certain planets and stars undergoing...

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