Emil Fischer and the Structure of -Glucose

Emil Fischer s determination of the structure of glucose was carried out as the nineteenth century ended and the twentieth began. The structure of no other sugar was known at that time, and the spectroscopic techniques that now aid organic analysis were not yet available. All Fischer had was information from chemical transformations, polarimetry, and his own intellect. 

Fischer knew that (+)-glucose was one of 16 possible stereoisomers having the constitution  

By arbitrarily assigning a particular configuration to the chirality center at C-5, Fischer realized that he could determine the configurations of C-2, C-3, and C-4 relative to C-5. This reduces the number of structural possibilities to the eight that we now call D-hexoses. 

Eventually, Fischer s arbitrary assignment proved correct, which made his stereochemical assignments for all of the chirality centers of (+)-glucose correct in an absolute as well as a relative sense. 

This fact is established in Problem 23.46 but used in Problem 23.45. 

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Descriptive Passage and Interpretive Problems 23 Emil Fischer and the Structure of (+)-Glucose 989... 

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