HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1928680Generated: October 30, 2026
2-Methylbenzenesulfonic acid → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one
https://huagongshe.com/reaction/1928680
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Methylbenzenesulfonic acid | HCID 6925 | — |
| Reactant | Trimethyl orthoformate | HCID 9005 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)-tetrahydropyran-2-one | HCID 44128178 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one | HCID 68898127 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08183397B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-2b9c94e5ab5b4cbdbbbae93991388f17 |
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| Source note | uspto-grants-2012_05 |
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