Synthesis of d-erythroascorbic acid from d-glucose

✍ Scribed by Li-Xian Gan; Paul A. Seib

• Publisher: Elsevier Science
• Year: 1991
• Tongue: English
• Weight: 721 KB
• Volume: 220
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(91)80010-k

✦ Synopsis

Reaction of a 4: 1 mixture of D-ribono-and D-arabinono-I ,4-lactones with benzaldehyde and hydrochloric acid gave 59% crystalline 3,4-O-benzyhdene-D-ribono-1,5-lactone.

This acetal was oxidized with manganese dioxide in acetone to its 2-keto derivative (6) in 76% yield. Acid-catalyzed methanolysis of 6 gave a syrupy mixture of products, which upon tautomerization in hot methanolic sodium acetate followed by removal of sodium ions gave 78% D-erythroascorbic acid (7). The overall yield of 7 starting from D-glucose was 20%.