Abstract
Saccharinic acids, branched 2- C-methyl-aldonic acids, may be accessed via a green procedure from aldoses by sequential conversion to an Amadori ketose and treatment with calcium hydroxide; d-galactose and d-glucose are converted to 2- C-methyl- d- lyxono-1,4-lactone (with a small amount of 2- C-methyl- d- xylono-1,4-lactone) and 2- C-methyl- d- ribono-1,4-lactone. Inversion of configuration at C-4 of the branched lactones allows access to 2- C-methyl- l- ribono-1,4-lactone and 2- C-methyl- l- lyxono-1,4-lactone, respectively. d-Xylose affords 2- C-methyl- d- threono-1,4-lactone and 2- C-methyl- d- erythrono-1,4-lactone, whereas l-arabinose, under similar conditions, gave the enantiomers 2- C-methyl- l- threono-1,4-lactone and 2- C-methyl- l- erythrono-1,4-lactone.
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