Benzyl Bromide → HCID 86668481, compound

HRID 1944085Notes

Reaction equation

HRID 1944085 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][O:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:9]2)=[CH:4][C:3]=1[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=1.[H-].[Na+].[CH2:50](Br)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-].O>[CH2:50]([O:14][C@@H:13]1[C@@H:12]([O:15][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:11]([O:16][CH2:38][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[C@@H:10]([CH2:17][O:18][C:19]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:9][C@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([O:45][CH2:46][CH3:47])=[CH:43][CH:44]=2)[CH:4]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 67074199HCID 67074199, compound

Product 1

HCID 86668481HCID 86668481, compoundYield 178%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,3R,4R,5S,6R)-2-[4-Chloro-3-(4-ethoxy-benzyl)-phenyl]-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol (9.8 g, 15 mmole) in dry DMF (50 mL), sodium hydride (3.2 g, 67.8 mmole) was added at 0° C. and stirred at room temperature for 2 hours. Benzyl bromide (5.9 mL, 49.7 mmole), TBAI (500 mg) were added and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with water (500 mL) and extracted with DCM (2×500 mL). The crude product obtained after removal of solvent to furnish 12.3 g of (2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-trityloxymethyl-tetrahydro-pyran.

Workup

  1. stirringthe reaction mixture stirred at room temperature for 18 hours
  2. extractionextracted with DCM (2×500 mL)
  3. customThe crude product obtained
  4. customafter removal of solvent

Sources & evidence

ORD record
ord-5ef89e0410b241b0b3b45491613ee21d
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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