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

HRID 1469208Notes

Reaction equation

HRID 1469208 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[CH3:24])[O:7][C@@H:6]1[CH2:35][O:36]C(=O)C)(=O)C.C[O-].[Na+].CC(O)=O>CO>[CH2:33]([C:30]1[CH:31]=[CH:32][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]([CH3:24])[C:22]=2[CH3:25])=[CH:28][CH:29]=1)[CH3:34]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 66693992(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Product 1

HCID 56670175(2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolYield 28.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (57) (125 mg, 0.223 mmole) in MeOH (5 mL) was added NaOMe (25 wt % in MeOH, 310 μL, 1.34 mmole). The reaction mixture was stirred at ambient temperature for 2 h before AcOH (2 mL) was added. Purification by reverse phase preparative HPLC provided the title compound 60 (24.8 mg, 0.0632 mmole, 28%) as a brown solid.

Workup

  1. additionwas added
  2. customPurification by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-40eef8a5b583452099e2e6b749b7106a
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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