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Formylation of primary hydroxyl groups in sugars

✍ Scribed by Li-Xian Gan; Roy L. Whistler

Publisher: Elsevier Science
Year: 1990
Tongue: English
Weight: 373 KB
Volume: 206
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(90)84006-g

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✦ Synopsis

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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