Acetic Acid → (2R,3R,4S,5S,6R)-2-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

HRID 1469206Notes

Reaction equation

HRID 1469206 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@H:8]([C:19]2[S:20][C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][CH:28]=3)=[C:22]([CH3:25])[C:23]=2[Br:24])[O:7][C@@H:6]1[CH2:35][O:36]C(=O)C)(=O)C.C[O-].[Na+].CC(O)=O>CO>[Br:24][C:23]1[C:22]([CH3:25])=[C:21]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([CH2:33][CH3:34])=[CH:31][CH:32]=2)[S:20][C:19]=1[C@H:8]1[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:35][OH:36])[O:7]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 66695439(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

Product 1

HCID 54597682(2R,3R,4S,5S,6R)-2-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of acetate (56) (200 mg, 0.320 mmol) in MeOH (5 mL) was added NaOMe (25 wt % in MeOH, 0.1 mL) at room temperature. The mixture was stirred at room temperature for 1 hr. Glacial AcOH was added to the mixture to acidify the mixture. The mixture was concentrated under reduced pressure. The residue was purified by prep HPLC (C18) to provide the title compound 58 (80 mg, 55%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-4c5cd2be0dd147aaa6a7f40ede5e31b4
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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