2-Methylbenzenesulfonic acid → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one

HRID 1928680Notes

Reaction equation

[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13](C(O)O)[O:12][C:11](=[O:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH:30]([O:35][CH3:36])([O:33][CH3:34])OC.C([O-])(O)=O.[Na+]>ClCCl>[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13]([CH:30]([O:33][CH3:34])[O:35][CH3:36])[O:12][C:11](=[O:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 1.0 g of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)-tetrahydropyran-2-one (V′) in 100 mL of dichloromethane, 50 mg of toluenesulfonic acid and 4.5 mL of trimethyl orthoformate are added. After 2 hours of stirring at 25° C., 0.2 g of NaHCO3 is added and dichloromethane is distilled off. The residue is flash chromatographed (MTBE/hexane 1/1) and the solvents are distilled off to get the title compound.

Workup

distillationdichloromethane is distilled off
customchromatographed (MTBE/hexane 1/1)
distillationthe solvents are distilled off

Sources & evidence

ORD record: ord-2b9c94e5ab5b4cbdbbbae93991388f17
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183397B2

Reaction notes

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