m-Chloroperbenzoic acid → 1-deoxy-1-(phenylsulfinyl)-2,3,4,6-tetra-O-pivaloyl-beta-D-galactopyranose

HRID 1637430Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of thioglycoside 40 (0.62 g, 1.0 mmol) in 20 mL of CH2Cl2 at -78° C. is added 67% m-CPBA (0.26 g, 1.0 mmol). The reaction mixture is stirred at -78° C. for 2 h and then allowed to slowly warm up to room temperature. Saturated NaHCO3 is added until the solution is basic. The reaction mixture is diluted with 100 mL of CH2Cl2 and washed with H2O (100 mL), saturated NaCl (100 mL), dried over Na2SO4, filtered, concentrated and purified by flash chromatography (15% EtOAc/hexane) to give 0.59 g (92%) of the title compound 41 as a mixture of diastereomers: Rf 0.38, 0.19 (20% EtOAc/hexane). FABMS C32H48O10S (MNa+) calcd 647.2866, found 647.2868.

Workup

temperatureto slowly warm up to room temperature
washwashed with H2O (100 mL), saturated NaCl (100 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by flash chromatography (15% EtOAc/hexane)

Sources & evidence

ORD record: ord-73db12818b7a451ebb4193f8b49e4fd5
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040433

Reaction notes

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