HCID 68740990, compound → HCID 21961232, compound

HRID 1445331Notes

Reaction equation

HRID 1445331 reaction equation
[OH:1][CH2:2][CH:3]1[CH:8]([OH:9])[CH:7]([OH:10])[CH:6]([OH:11])[CH:5]([O:12][C:13]2[CH:17]=[CH:16][S:15][C:14]=2[CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[O:4]1>CO.[Pd]>[OH:1][CH2:2][CH:3]1[CH:8]([OH:9])[CH:7]([OH:10])[CH:6]([OH:11])[CH:5]([O:12][C:13]2[CH:17]=[CH:16][S:15][C:14]=2[CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[O:4]1

Participants

4

Reactant 1

HCID 68740990HCID 68740990, compound

Product 1

HCID 21961232HCID 21961232, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

50 mg 2-hydroxymethyl-6-{2-[2-(4-methoxy-phenyl)-vinyl]-thiophen-3-yloxy}-tetrahydro-pyran-3,4,5-triol were dissolved in 10 of methanol. 20 mg of palladium on activated carbon were added and the solution was stirred under a hydrogen atmosphere for 18 h. The catalyst was filtered off and washed with 60 ml of methanol, and the organic phase was concentrated. The residue was chromatographed on silica gel (ethyl acetate). 18 mg of the product with the molecular weight of 396.46 (C19H24)7S); MS (ESI): 419.05 (M+Na+), 414.10 (M+NH4+).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with 60 ml of methanol
  3. concentrationthe organic phase was concentrated
  4. customThe residue was chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-6b380945005e415e9aca8b5a15e16d1e
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Reaction notes

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