Methanol → HCID 10950146, compound

HRID 858167Notes

Reaction equation

HRID 858167 reaction equation
[O:1]([CH3:11])[CH:2]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:5]([OH:6])[C@@H:3]1O.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:22][OH:23]>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:22]([O:23][C@H:3]1[C@H:5]([O:6][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:7]([CH2:9][O:10][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH:2]1[O:1][CH3:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18637782Methyl D-arabinofuranoside

Product 1

HCID 10950146HCID 10950146, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of 2 (10 g, 60.9 mmol) in dry tetrahydrofuran (350 mL) was added sodium hydride (60% dispersion in mineral oil, 14.8 g, 370 mmol) and the reaction mixture was stirred for 15 min under N2. To this reaction mixture was added solid tetrabutylammonium iodide (0.36 g, 0.96 mmol) followed by a dropwise addition of benzyl bromide (36.6 g, 214 mmol). The reaction mixture was stirred for 3 days at room temperature. After the addition of methanol (25 mL), the solution was evaporated under reduced pressure, and the crude product was purified by silica gel chromatography (cyclohexane/EtOAc, 9:1) to afford pure methyl 2,3,5-tri-O-benzyl-D-arabinofuranoside (3, 23 g, 87% yield). MS 435 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 3 days at room temperature
  2. customthe solution was evaporated under reduced pressure
  3. customthe crude product was purified by silica gel chromatography (cyclohexane/EtOAc, 9:1)

Sources & evidence

ORD record
ord-c3b9ee2ed48541cd9e71883c3ee2e4d6
Source dataset
uspto-grants-2006_12
Patent number
US07148223B2

Reaction notes

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