Draw the mechanism of the reactions of steps 1 and 2

[physicisttobe]

Homework Statement

Tetramethylguanidine/monomethoxytrityl

Relevant Equations

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Hi everyone!

There is a task that I can't solve. Can you explain me how I have to draw the full mechanism?

Draw the mechanism of the reactions of step 1 and 2. Indicate the product before step
3. (in step 2 also TMG =Tetramethylguanidine is given and instead of the
protecting group DMT was given MMT =monomethoxytrityl).

 

[TeethWhitener]

You need to show some work before we can help you. Maybe start by identifying which reagent deprotects which functional group.

 

[physicisttobe]

Oh yes, next time i will post all my approaches. I was a little uncertain, whether the mechanism is correct. Therefore, I did not upload anything.
But my approach looks like this. I hope it‘s correct:

 

[TeethWhitener]

It looks like you have the idea. A couple of minor things: make sure the protecting groups you aren’t removing stay on the diagrams, and make sure the protecting groups you’ve already removed don’t (for instance, in the mechanism for step 2, you still have the DMT group protecting the sugar OH, which you just showed was removed in step 1). There’s one or two other little errors of that nature, but overall, the mechanism looks pretty good.

 

[physicisttobe]

All right, thanks a lot!!