What do parenthesis mean in a fischer projection?

[NuttyEngDude]

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Hello.

What do parenthesis mean in a fischer projection? For example, in compound X below the OH's on the right carbon position 2,3, and 4 have parenthesis. Does this mean they are not really on the right hand side of the fischer projection? notice the OH attached to the 5th carbon does not have parenthesis.

for example:

Thanks!

edit: This is from TBR ochem carbohydrates chapter passage 7 (if you are worried about spoilers)

 

[BerkReviewTeach]

Hello.

What do parenthesis mean in a fischer projection? For example, in compound X below the OH's on the right carbon position 2,3, and 4 have parenthesis. Does this mean they are not really on the right hand side of the fischer projection? notice the OH attached to the 5th carbon does not have parenthesis.

for example:

Thanks!

edit: This is from TBR ochem carbohydrates chapter passage 7 (if you are worried about spoilers)

It means that the stereochemistry at that carbon is uncertain. So in that example, three of the four chiral centers (carbons 2, 3, and 4) have the OH on either the left or the right.

For what it's worth, BTW, that passage has been removed and replaced in the latest BR books.

 

[NuttyEngDude]

Thank you! 🙂