HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 339150Generated: October 29, 2026
Imidazole → (2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester
https://huagongshe.com/reaction/339150
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | 2,6-Lutidine | HCID 7937 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | (R)-2-((R)-3-benzyloxy-1-hydroxypropyl)pent-4-enoic acid methyl ester | HCID 67234162 | — |
| Reactant | (Tert-butoxy)dimethylsilane | HCID 71403863 | — |
| Catalyst | Osmium Tetroxide | HCID 30318 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | (2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester | HCID 86654300 | 88% |
Reaction Steps
The compound obtained in example 3e was protected as the tert-butyl dimethyl silyl ether by treatment with tert-butyldimethylchlorosilane and imidazole in DMF. This compound was treated with 2,6-lutidine and OsO4 2.5% in 2-methyl-2-propanol, followed by NalO4 in 1,4-dioxane-water (3:1) at room temperature. The reaction was stirred at 25° C. for 2 hrs, quenched, and the product purified by chromatography to provide (2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester in 88% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08889894B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-595e3ad2f37746c487f9b5e285d3e241 |
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| Source note | uspto-grants-2014_11 |
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