[skystem10]

Hello,

For my medical chemistry lab the professor gave us a compound used in the clinical (bexagliflozin) and we have to search about their synthesis and mechanism.
I can't comprehend what is going on here. I've been all afternoon looking around different mechanisms but i can't seem to understand it at all.
What im thinking is that the organolithium (of our choice, let's suppose it's nBu-Li) acts as a nucleophile but how does the condensation between the TMSO glucoside and the other molecule combines.

I hope someone can understand my question, i have to get this done by next week.

Thank u.

[Babcock_Hall]

I suggest that you think about alternative ways in which nBuLi might react.

[rolnor]

X must be Br or I? You already have a Cl in the molecule? F will not work for sure.

[clarkstill]

It might help to first consider the reaction between n-BuLi and molecule A, before the addition of B.

[skystem10]

It might help to first consider the reaction between n-BuLi and molecule A, before the addition of B.

I thought about nucleophilic substitution between nBuLi and A and then A with Li in X attacks B. Is that correct?

[rolnor]

What do you know about BuLi? What is it used for? Not nucleophilic substitution, for sure.

https://en.wikipedia.org/wiki/N-Butyllithium