March 05, 2024, 08:51:00 AM
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Topic: Mechanism of reaction  (Read 1093 times)

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Offline skystem10

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Mechanism of reaction
« 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.

Offline Babcock_Hall

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Re: Mechanism of reaction
« Reply #1 on: May 30, 2023, 01:18:17 PM »
I suggest that you think about alternative ways in which nBuLi might react.

Offline rolnor

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Re: Mechanism of reaction
« Reply #2 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.

Offline clarkstill

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Re: Mechanism of reaction
« Reply #3 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.

Offline skystem10

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Re: Mechanism of reaction
« Reply #4 on: June 04, 2023, 02:45:36 PM »
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?

Offline rolnor

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Re: Mechanism of reaction
« Reply #5 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

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