m-Chloroperbenzoic acid → HCID 70250422, compound

HRID 1637422Notes

Reaction equation

[C:1]([O:9][C@H:10]1[C@@H:22]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:21]([CH3:32])[O:20][C@H:12]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:11]1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:51])C=1>C(Cl)Cl>[C:1]([O:9][C@H:10]1[C@@H:22]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:21]([CH3:32])[O:20][C@H:12]([S:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:51])[C@H:11]1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of phenyl 6-deoxy-3,4-di-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-allopyranoside (β-13, prepared above) (400 mg, 0.7 mmol) in 10 mL of CH2Cl2 at -78° C. is added a solution of mCPBA (170 mg, 1.1 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 nL), dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography (EtOAc/petroleum ether) to give 1,6-dideoxy-3,4-di-O-benzoyl-2-O-(4-methoxybenzyl)-1-(phenylsulfinyl)-β-L-allopyranose as a mixture of diastereomers.

Workup

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

Sources & evidence

ORD record: ord-8587ee6f8571418497ae48cd847572bc
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040433

Reaction notes

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