Toluene → (3R,4S,5R,6R)-3,4,5-Tris-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-on
Reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[OH:6][C@@H:7]1[C@@H:12]([OH:13])[C@H:11]([OH:14])[C@@H:10]([CH2:15][OH:16])[O:9][C:8]1=[O:17].CN1CCOCC1.C1(C)C=CC=CC=1>C1COCC1.O>[CH3:1][Si:2]([CH3:4])([CH3:3])[O:6][C@@H:7]1[C@@H:12]([O:13][Si:2]([CH3:4])([CH3:3])[CH3:1])[C@H:11]([O:14][Si:2]([CH3:4])([CH3:3])[CH3:1])[C@@H:10]([CH2:15][O:16][Si:2]([CH3:4])([CH3:3])[CH3:1])[O:9][C:8]1=[O:17]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
At −7° C., TMSCl (71 mL) was added into a solution of (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one (14.2 g) and N-methylmorpholine (80 mL) in dry THF (120 mL), and then the mixture was slowly warmed up to room temperature and stirred overnight. At 10° C., toluene (160 mL) and H2O (300 mL) were poured into the mixture, and then the organic phase was washed with H2O (120 mL), 1M HCl (150 mL×4) and brine (120 mL). The organic phase was dried over Na2SO4, and concentrated to obtain the crude product, then the crude product was purified by silica-gel column chromatography (PE/EA=10/1) to obtain 30 g of (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one.
Workup
- washthe organic phase was washed with H2O (120 mL), 1M HCl (150 mL×4) and brine (120 mL)
- dry with materialThe organic phase was dried over Na2SO4
- concentrationconcentrated
- customto obtain the crude product
- customthe crude product was purified by silica-gel column chromatography (PE/EA=10/1)
Sources & evidence
- ORD record
- ord-aef39ebddc3b45d480c4293322bd4f1a
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957033B2
Reaction notes
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