Tetrabutylammonium Periodate → (4r)-4-Benzyl-3-[(2s,3s,4r)-2-methyl-3-hydroxy-4-p-methoxybenzyloxyhex-5-enoyl]-2-oxazolidinone

HRID 392842Notes

Reaction equation

[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:39])[C@@H:15]([CH3:38])[C@H:16]([OH:37])[C@H:17]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH2:18][CH:19]([SeH])C1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([C@@H]1COC(=O)N1C(=O)[C@H](C)[C@@H](O)[C@H](OCC1C=CC(OC)=CC=1)CC([SeH])C1C=CC=CC=1)C1C=CC=CC=1.I([O-])(=O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)(Cl)Cl>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:39])[C@@H:15]([CH3:38])[C@H:16]([OH:37])[C@H:17]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH:18]=[CH2:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

2.41 g (4.0 mmol, 1.0 eq) of a 7/3 mixture of (4R)-4-benzyl-3-[(2S,3S,4R)-2-methyl-3-hydroxy-4-p-methoxybenzyloxy-6-phenylselenylhexanoyl]-2-oxazolidinone and (4R)-4-benzyl-3-[(2R,3R,4R)-2-methyl-3-hydroxy-4p-methoxybenzyloxy-6-phenylselenylhexanoyl]-2-oxazolidinone are dissolved in 25 mL of chloroform in the presence of 2.45 g (5.6 mmol, 1.4 eq) of tetrabutylammonium periodate. The reaction is stirred at 65° C. for three hours. The chloroform is evaporated off and the residue is then chromatographed on silica gel: eluent (7/3 Cy/EtOAc).

Workup

customThe chloroform is evaporated off
customthe residue is then chromatographed on silica gel

Sources & evidence

ORD record: ord-47f222a66d5341abaf739f77affadb46
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803382B2

Reaction notes

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