HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1928681Generated: November 1, 2026
Potassium Sodium Tartrate → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2-ol
https://huagongshe.com/reaction/1928681
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Sodium Tartrate | HCID 9357 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one | HCID 68898127 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2-ol | HCID 69184843 | — |
Reaction Steps
A solution of 0.6 g of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one (III′) in 36 mL of dichloromethane is cooled to −78° C. after 2 mL of DIBALH (25% in toluene) are added over 10 minutes. After 1 hour of stirring at −78° C., 0.9 g of Rochelle salt in 60 mL of water are added, phases are separated 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-671d65f9577e43a8ac53a4db486aa355 |
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| Source note | uspto-grants-2012_05 |
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