Benzoyl chloride → 2,3,5-tri-O-benzoyl-1-O-methyl-L-ribofuranose

HRID 1944794Notes

Reaction equation

HRID 1944794 reaction equation
[CH3:1][O:2][CH:3]1[O:9][C@@H:8]([CH2:10][OH:11])[C@H:6]([OH:7])[C@@H:4]1[OH:5].[OH-:12].[Na+].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:14]([O:5][C@H:4]1[C@@H:6]([O:7][C:14](=[O:12])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:8]([CH2:10][O:11][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:9][CH:3]1[O:2][CH3:1])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide2×HCID 11008257L-Ribofuranoside, methyl2×

Product 1

HCID 110162552,3,5-tri-O-benzoyl-1-O-methyl-L-ribofuranose

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Procedure

31.18 g of the crude 1-O-methyl-L-ribofuranose synthesized in (1) above, toluene (175 ml), a 25 wt. % sodium hydroxide aqueous solution (111 ml), and tetra-normal-butyl ammonium bromide (1.20 g; 5 molar % ratio) were added to a 1-L flask. The obtained mixture was cooled to an ice-cooled temperature, and benzoyl chloride (56.6 mol; 3.05 equivalents) was then slowly added dropwise thereto. The temperature was increased to room temperature, and the reaction was then carried out for 2 hours. The reaction product was again cooled to an ice-cooled temperature, and it was then diluted with toluene (200 ml) and a 1 N sodium hydroxide aqueous solution (100 ml). The temperature was increased to room temperature, and an organic layer was separated from an aqueous layer. The organic layer was washed with a 1 N sodium hydroxide aqueous solution (100 ml) 2 times, and was then washed with a 3 N hydrochloric acid aqueous solution (200 ml), so that the organic layer was concentrated. Thus, 62.69 g of crude 2,3,5-tri-O-benzoyl-1-O-methyl-L-ribofuranose was obtained in the form of a colorless oily liquid.

Workup

  1. additionwas then slowly added dropwise
  2. temperaturecooled temperature, and it
  3. temperatureThe temperature was increased to room temperature
  4. customan organic layer was separated from an aqueous layer
  5. washThe organic layer was washed with a 1 N sodium hydroxide aqueous solution (100 ml) 2 times
  6. washwas then washed with a 3 N hydrochloric acid aqueous solution (200 ml), so that the organic layer
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-5156c256d0454c29817a915181febca6
Source dataset
uspto-grants-2013_03
Patent number
US08394935B2

Reaction notes

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