Cesium carbonate → (2S,3R,4R,5S,6R)-2-(3-(4-(2-(2-bromoethoxy)ethoxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

HRID 425079Notes

Reaction equation

HRID 425079 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]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38]Br>CN(C)C=O.O>[Br:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:3]2[CH:4]=[C:5]([C@H:8]3[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]3)[CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 21521Bis(2-bromoethyl) etherHCID 44580555Bms-5119262×

Product 1

HCID 59557753(2S,3R,4R,5S,6R)-2-(3-(4-(2-(2-bromoethoxy)ethoxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolYield 21.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (intermediate D1) (100 mg, 0.26 mmol) in N,N-dimethylformamide (3 mL) and cesium carbonate (162 mg, 0.52 mmol) was added 1-bromo-2-(2-bromoethoxy)ethane (182 mg, 0.79 mmol). The mixture was stirred overnight at room temperature. The solution was diluted with water and the aqueous layer was extracted with ethyl acetate. The combined organic layers were concentrated under reduced pressure. The residue was purified by preparative TLC to give 30 mg of yellow oil (21% yield), which was used in the next step without purification.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. concentrationThe combined organic layers were concentrated under reduced pressure
  3. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-be4e15b5e31c427bad6da1711471ccd0
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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