Formylation of primary hydroxyl groups in sugars.
Application of 99% formic acid at 25 degrees formylates primary hydroxyl groups as shown by the easy formation of 6-O-formyl-D-glucopyranose and 6-O-formyl-D-fructofuranose, isolated as their tetra-acetates in yields of 77% and 31%, respectively. Likewise, D-glucitol gave the 2,3,4,5-tetra-O-acetyl-1,6-di-O-formyl derivative (84%) and methyl alpha-D-glucopyranoside gave the 6-formate (74%) characterized as the crystalline triacetate. On storage of the triacetate in methanol at 25 degrees, the formyl group was lost and the 2,3,6-triacetate was formed, whereas the corresponding tribenzoate was deformylated in acidic methanol without migration of the benzoyl groups.
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Whistler Center of Carbohydrate Research, Purdue University, West Lafayette, Indiana 47907.
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D002241:Carbohydrates / Q000737:chemistry*; D005561:Formates; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D002241:Carbohydrates; D005561:Formates; C030544:formic acid