(3R,4S,5R,6R)-3,4,5-Tris-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-on → delta-Gluconolactone
Reaction equation
C[Si](C)(C)[O:3][C@@H:4]1[C@@H:9]([O:10][Si](C)(C)C)[C@H:8]([O:15][Si](C)(C)C)[C@@H:7]([CH2:20][O:21][Si](C)(C)C)[O:6][C:5]1=[O:26]>CCCCCCC>[CH2:20]([OH:21])[C@H:7]1[O:6][C:5](=[O:26])[C@H:4]([OH:3])[C@@H:9]([OH:10])[C@@H:8]1[OH:15]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -26 °C
Procedure
All procedures except those explicitly stated were carried out under nitrogen. (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one (15.114 kg) was charged to a 40 L cryogenic reactor and heptane mixture of isomers (26 L, petroleum ether 90-100° C. fraction) was added and the solution was cooled to −26° C.
Workup
- additionwas added
Sources & evidence
- ORD record
- ord-7a14e9fbca1e4143bac534b7bdf200ef
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193751B2
Reaction notes
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