Hydrogen Peroxide → HCID 59431064, compound

HRID 2261200Notes

Reaction equation

HRID 2261200 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([S:17]([CH2:20][CH3:21])(=O)=[O:18])[O:9]2)=[CH:4][C:3]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=1.ClC1C=CC([C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](SCC)O2)=CC=1CC1C=CC(OCC)=CC=1.OO>CC(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([S:17]([CH2:20][CH3:21])=[O:18])[O:9]2)=[CH:4][C:3]=1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH3:31])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 24831713HCID 24831713, compoundHCID 66884446HCID 66884446, compound2×

Product 1

HCID 59431064HCID 59431064, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Preparation of (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-ethanesulfonyl-tetrahydro-pyran-3,4,5-triol and (2S,3R,4R,5S,6R)-2-[4-Chloro-3-(4-ethoxy-benzyl)-phenyl]-6-ethanesulfonyl-tetrahydro-pyran-3,4,5-triol. To a solution of compound from step A (10 mg, 0.023 mmol) in AcOH (0.5 ml) was added H2O2 (35 wt % solution in H2O, 3 mg, 0.092 mmol, 9 μl). The mixture was stirred at ambient temperature for 2 hours before being concentrated under vacuum. Purification of the mixture by silica gel chromatography (5% MeOH/CH2Cl2) afforded (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-ethanesulfinyl-tetrahydro-pyran-3,4,5-triol (as a mixture of diastereomers at sulfur) (2 mg, 19%) and (2S,3R,4R,5S,6R)-2-[4-Chloro-3-(4-ethoxy-benzyl)-phenyl]-6-ethanesulfonyl-tetrahydro-pyran-3,4,5-triol (5 mg, 46%) both as white solids.

Workup

  1. concentrationbefore being concentrated under vacuum
  2. customPurification of the mixture by silica gel chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-bb236f88d98442eab25387342c09884b
Source dataset
uspto-grants-2010_12
Patent number
US07846945B2

Reaction notes

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