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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: skystem10 on May 29, 2023, 11:45:12 PM

Title: Mechanism of reaction
Post by: skystem10 on May 29, 2023, 11:45:12 PM

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.

Title: Re: Mechanism of reaction
Post by: Babcock_Hall on May 30, 2023, 01:18:17 PM

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

Title: Re: Mechanism of reaction
Post by: rolnor on June 01, 2023, 04:34:41 PM

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

Title: Re: Mechanism of reaction
Post by: clarkstill on June 02, 2023, 07:26:46 AM

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

Title: Re: Mechanism of reaction
Post by: skystem10 on June 04, 2023, 02:45:36 PM

Quote from: clarkstill on June 02, 2023, 07:26:46 AM

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?

Title: Re: Mechanism of reaction
Post by: rolnor on June 05, 2023, 08:31:46 AM

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

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