Sodium Methoxide → (2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3-methoxy-4-methylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

HRID 1469207Notes

Reaction equation

HRID 1469207 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]=2Br)[O:7][C@@H:6]1[CH2:35][O:36]C(=O)C)(=O)C.[CH3:40][O-:41].[Na+]>>[CH2:33]([C:30]1[CH:29]=[CH:28][C:27]([CH2:26][C:21]2[S:20][C:19]([C@H:8]3[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:35][OH:36])[O:7]3)=[C:23]([O:41][CH3:40])[C:22]=2[CH3:25])=[CH:32][CH:31]=1)[CH3:34]

Participants

3

Reactant 2

HCID 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 56666748(2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3-methoxy-4-methylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolYield 19%

Conditions

Temperature
120 °C

Procedure

To a solution of (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 (56) (200 mg, 0.320 mmole) in NaOMe (25 wt % in MeOH, 10 mL, 43.2 mmole) were added cupric oxide (25.5 mg, 0.320 mmole) and KI (53.1 mg, 0.320 mmole). The resulting solution was stirred at 120° C. overnight. The reaction mixture was filtered through Celite® bed and concentrated in vacuo. The crude residue was purified on reverse phase preparative HPLC to yield the title compound 59 (24.3 mg, 0.0595 mmole, 19%) as a yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite® bed
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified on reverse phase preparative HPLC

Sources & evidence

ORD record
ord-a4b4548d1bc6404092de9f4a4789db0a
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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