1-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-ulose → Methyl 3,5-bis-O-((2,4-dichlorophenyl)methyl)-2-C-methyl-alpha-D-ribofuranoside

HRID 1245507Notes

Reaction equation

HRID 1245507 reaction equation
[CH3:1][Mg+].[Br-].[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[CH2:12][O:13][C@@H:14]1[C@@H:20]([CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])[O:19][C@H:16]([O:17][CH3:18])[C:15]1=[O:32]>CCOCC>[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[CH2:12][O:13][C@@H:14]1[C@@H:20]([CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])[O:19][C@H:16]([O:17][CH3:18])[C@:15]1([CH3:1])[OH:32]

Participants

4

Reactant 2

HCID 113750391-O-Methyl-3,5-bis-O-[(2,4-dichlorophenyl)methyl]-alpha-D-erthro-pentofuranoside-2-uloseHCID 178418689HCID 178418689, compound

Product 1

HCID 11283339Methyl 3,5-bis-O-((2,4-dichlorophenyl)methyl)-2-C-methyl-alpha-D-ribofuranoside

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a solution of MeMgBr in anhydrous Et2O (0.48 M, 300 mL) at −55° C. was added dropwise a solution of the compound from Step B (17.40 g, 36.2 mmol) in anhydrous Et2O (125 mL). The reaction mixture was allowed to warm to −30° C. and stirred for 7 h at −30° C. to −15° C., then poured into ice-cold water (500 mL) and the mixture vigorously stirred at room temperature for 0.5 h. The mixture was filtered through a Celite pad (10×5 cm) which was thoroughly washed with Et2O. The organic layer was dried (MgSO4), filtered and concentrated. The residue was dissolved in hexanes (˜30 mL), applied onto a silica gel column (10×7 cm, prepacked in hexanes) and eluted with hexanes and hexanes/EtOAc (9/1) to give the title compound (16.7 g) as a colorless syrup.

Workup

  1. stirringthe mixture vigorously stirred at room temperature for 0.5 h
  2. filtrationThe mixture was filtered through a Celite pad (10×5 cm) which
  3. washwas thoroughly washed with Et2O
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in hexanes (˜30 mL)
  8. washeluted with hexanes and hexanes/EtOAc (9/1)

Sources & evidence

ORD record
ord-f849630b916d4e1aa47716d0240e1922
Source dataset
uspto-grants-2006_10
Patent number
US07125855B2

Reaction notes

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