(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → methyl alpha-D-glucopyranoside
Reaction equation
[CH3:1][O:2][C@@H:3]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@H:5]([OH:12])[C@H:4]1[OH:13].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>>[CH3:1][O:2][C@H:3]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@H:5]([OH:12])[C@H:4]1[OH:13]Participants
3
Procedure
In the above Table I, it can be seen tht Sample A product composition gave a yield of 79.0% methyl-alpha-D-glucopyranoside and methyl-beta-D-glucopyranoside, and only 10.81% of polyglycosides and dextrose. Sample D produced 77.12% methyl-alpha-D-glucopyranoside and methyl-beta-D-glucopyranoside, while Sample G produced only 71.55% of the glucosides. At the same time, the percentages of polyglycosides and dextrose increased as the methanol:starch ratio decreased. The cost of removal of excess methanol must be balanced against the slightly increased yield of glucosides.
Sources & evidence
- ORD record
- ord-d06364d58a3942d68d5dd882b80eecd0
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04223129
Reaction notes
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