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Topic: Problems with determining absolute configuration  (Read 1425 times)

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Offline Anthasci

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Problems with determining absolute configuration
« on: October 28, 2012, 11:44:38 AM »
I'm having troubles with this specific example of determining the absolute configuration of (the dots are just placeholders):

H2N
.,.,|
H-C-COOH
.,.,|
....COOEt

because none of the bonds are stereochemically determined (I'm guessing it's some sort of a Fischer transformation). Obviously, the priority goes as such: NH2 > COOEt > COOH > H and the H-atom bonded to the chiral C-atom is "in way" between H2N and COOEt and the molecule above would be S-oriented, which is false. My question here is, where am I supposed to put the H-atom? Probably out of the plane, but I can't just go around switching the sterical position of atoms, or can I?

Offline Anthasci

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Re: Problems with determining absolute configuration
« Reply #1 on: October 28, 2012, 12:16:59 PM »
Nevermind, I think I solved the issue. It's a wonder how putting out your thoughts helps the process of understanding. Now if anyone could just help me name this compound? I was thinking something along R-ethanoylalanine or maybe R-alaninylacetate, but I have strong doubts about that being correct

Offline discodermolide

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Re: Problems with determining absolute configuration
« Reply #2 on: October 28, 2012, 12:22:03 PM »
It's name is (R)-2-amino-3-ethoxy-3-oxopropanoic acid.
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