Dimethyl Sulfide → HCID 15460403, compound

HRID 1637417Notes

Reaction equation

[C:1]([O:7][C@H:8]1[C@H:20]([O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C@H:19]([O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C@H:18]([CH3:35])[O:17][C@@H:9]1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C1C=C(Cl)C=C(C(OO)=[O:44])C=1.CSC>C(Cl)Cl>[C:1]([O:7][C@H:8]1[C@H:20]([O:21][C:22](=[O:27])[C:23]([CH3:24])([CH3:25])[CH3:26])[C@H:19]([O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C@H:18]([CH3:35])[O:17][C@@H:9]1[S:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:44])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of phenyl 6-deoxy-2,3,4-tri-O-pivaloyl-1-thio-β-L-galactopyranoside 4 (2.47 g, 5.22 mmol) in 65 mL of CH2Cl2 at -78° C. is added mCPBA (1.53 g, 8.84 mmol). The reaction mixture is allowed to warm to -15° C. and then quenched with methyl sulfide (5.3 mL, 4.48 g, 17.4 mmol) and allowed to warm to room temperature. The reaction mixture is then diluted with 50 mL CH2Cl2, extracted with H2O (100 mL), saturated NaHCO3 (100 mL), saturated NaCl (100 mL), dried over Na2SO4, filtered and concentrated to afford a white solid. The sulfoxide is purified using flash chromatography (15% EtOAc/petroleum ether) to afford 1.81 g (66%) of 1,6-dideoxy-2,3,4-tri-O-pivaloyl-1-(phenylsulfinyl)-β-L-galactopyranose 5 as a mixture of diastereomers: Rf 0.05 and 0.13 (15% EtOAc/petroleum ether).

Workup

temperatureto warm to room temperature
extractionextracted with H2O (100 mL), saturated NaHCO3 (100 mL), saturated NaCl (100 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto afford a white solid
customThe sulfoxide is purified

Sources & evidence

ORD record: ord-351b3ca97e8441ab9d890faab6b5470b
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040433

Reaction notes

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