Imidazole → (2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester

HRID 1025255Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([C@H:8]([OH:19])[CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][CH:6]=C.C[SiH]([O:24]C(C)(C)C)C.[C:29]([Si:33]([CH3:36])([CH3:35])Cl)([CH3:32])([CH3:31])[CH3:30].N1C=CN=C1.N1C(C)=CC=CC=1C>CN(C=O)C.CC(O)(C)C.O1CCOCC1.O.O=[Os](=O)(=O)=O>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:5][CH:6]=[O:24])[C@H:8]([O:19][Si:33]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:36])[CH3:35])[CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

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.

Workup

customquenched
customthe product purified by chromatography

Sources & evidence

ORD record: ord-ad6901e5134345ce9dd889a19c07290e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08728515B2

Reaction notes

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