Carbohydrate Research p. 117 - 126 (1991)
Update date:2022-08-05
Topics:
Gan, Li-Xian
Seib, Paul A.
Reaction of a 4:1 mixture of D-ribono- and D-arabinono-1,4-lactones with benzaldehyde and hydrochloric acid gave 59percent crystalline 3,4-O-benzylidene-D-ribono-1,5-lactone.This acetal was oxidized with manganese dioxide in acetone to its 2-keto-derivative (6) in 76percent 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 78percent D-erythroascorbic acid (7).The overall yield of 7 starting from D-glucose was 20percent.
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Doi:10.1021/jo00032a046
(1992)Doi:10.1002/asia.201200182
(2012)Doi:10.1039/c2ob25923k
(2012)Doi:10.1016/j.tetlet.2017.09.016
(2017)Doi:10.1007/s10600-019-02724-5
(2019)Doi:10.1002/hlca.19910740836
(1991)
