Potassium Hydroxide → Potassium D-lyxonate
Reaction equation
O=C[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[OH-:13].[K+:14]>>[O:13]=[C:3]([O-:4])[C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6].[K+:14]Participants
3
Procedure
The multi-step synthesis from D-galactose comprises oxidizing the D-galactose in KOH solution to open the pyranose ring and form potassium D-lyxonate, subjecting the latter compound to alcoholic solution under acid conditions to provide furanose ring closure and form the D-lyxono-1,4-lactone, and then introducing a protecting group at C-2 and C-3 by reaction with ketone in the presence of a dehydrating agent. Use of acetone as the ketone in the latter step gives the compound 2,3-0-isopropylidene-D-lyxono-1,4-lactone. From that point on the multi-step system includes the general reaction steps of the above short synthesis.
Sources & evidence
- ORD record
- ord-d59305c460654965ba0a7bd0ce9a1a6e
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04910310
Reaction notes
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