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Author: Subject: Synthesis Review
jarodduesing
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[*] posted on 26-1-2022 at 17:39
Synthesis Review


Hello, I hope you are having a fantastic new year so far. We are planning to synthesize this and would like to know what you think of the pathway. There are 2 precursors being created as well. There is a kingdraw file and pictures of all the pathways. Do you think a stronger protecting agent will be needed on the oxygens? Thanks for sharing your time and expertise!

https://drive.google.com/drive/folders/1cmSQx5e3oDSnfWoWsWDx...

V3 Kingdraw and .png added since I lost carbon in my drawings :(

[Edited on 27-1-2022 by jarodduesing]
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Sigmatropic
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[*] posted on 26-1-2022 at 23:16


Just upload your scheme as one figure.
It is full of errors, where did you get this pathway from? It will not work as shown.
Step1: a peptide coupling with a boc protected amine wont work. Step2: 'protecting oxygens' those are carbonyl oxygens on an amide. Depending on the chemistry they usually dont need protection. I dont think they react with Et3SiH/TFA
Step3: theres a carbon missing
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jarodduesing
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[*] posted on 27-1-2022 at 04:18


Sigma,

Thank you so much for your advice! I was actually designing jt myself for the most part so that accounts for the errors :) For the peptide coupling on a secondary amine would the reaction only occur once, or would I need to protect with a different compound?
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