Question

Which is the preferred
configuration for the synthesis of
S-propanediol from aldohexose
with respective stereochemistry
at C2,C3,C4 and CS

Answer 1

The preferred configuration for the synthesis of S-propanediol from aldohexose with respective stereochemistry at C2,C3,C4 and C5 is R,S,S,R.

• A technique for manufacturing monosaccharides is called the Kiliani-Fischer synthesis after German chemists Heinrich Kiliani and Emil Fischer.
• The process starts with the manufacture and hydrolysis of a cyanohydrin, then reduces the intermediate acid to the aldehyde, lengthening the aldose's carbon chain by one carbon atom while maintaining the stereochemistry of all the chiral carbons that were already there.
• A Kiliani-Fischer synthesis results in a combination of two diastereomeric sugars known as epimers since the new chiral carbon can be created using both stereochemistries.
• As an illustration, D-arabinose is changed into a combination of D-glucose and D-mannose.

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