m-Chloroperbenzoic acid → HCID 15460405, compound

HRID 1637421Notes

Reaction equation

[N:1]([C@@H:4]1[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([CH3:26])[O:14][C@H:6]([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]1[O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[N+:2]=[N-:3].C1C=C(Cl)C=C(C(OO)=[O:42])C=1>C(Cl)Cl>[N:1]([C@@H:4]1[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@H:15]([CH3:26])[O:14][C@H:6]([S:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:42])[C@H:5]1[O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of phenyl 3-azido-4-O-benzoyl-3,6-di-deoxy-2-O-pivaloyl-1-thio-β-L-galactopyranoside (β-19) (270 mg, 0.575 mmol) in 10 mL of CH2Cl2 at -78° C. is added a solution of mCPBA (159 mg of 64% material, 0.920 mmol) in 2 mL of CH2Cl2. The reaction mixture is allowed to warm to -20° C. and then quenched with TEA (500 μL, 3.59 mmol). The reaction mixture is diluted with 10 mL of CH2Cl2. washed with saturated NaHSO3 (10 mL), saturated NaHCO3 (10 mL), dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography (60% EtOAc/petroleum ether) to give 231 mg (83%) of 3-azido-4-O-benzoyl1,3,6-tri-deoxy-2-O-pivaloyl-1-(phenylsulfinyl)-β-L-galactopyranose (β-20) as a mixture of diastereomers: Rf 0.26 (50% EtOAc/petroleum ether).

Workup

washwashed with saturated NaHSO3 (10 mL), saturated NaHCO3 (10 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product is purified by flash chromatography (60% EtOAc/petroleum ether)

Sources & evidence

ORD record: ord-51787e1d095d44f8861c14d2996a3fc6
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040433

Reaction notes

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