HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1928685Generated: October 30, 2026
Imidazole → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one
https://huagongshe.com/reaction/1928685
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | (4R,6S)-6-(dimethoxymethyl)-4-hydroxy-tetrahydropyran-2-one | HCID 67320619 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one | HCID 68898127 | — |
Reaction Steps
To a solution of 0.5 g of (4R,6S)-6-(dimethoxymethyl)-4-hydroxy-tetrahydropyran-2-one (II′) in 50 mL of dichloromethane, 280 mg of imidazole are added at 25° C. After cooling to 0° C., 400 mg of tert-butyldimethylsilyl chloride are added. The reaction mixture is then stirred for 18 hours and dichloromethane is distilled off. The residue is flash chromatographed (DIPE/acetonitrile=5/1). 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-abd12c52635e4ac5a7df41157829b8bc |
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| Source note | uspto-grants-2012_05 |
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