Methyl-2-o-acetyl-3,5-bis-o-(2,4-dichlorobenzyl)-1-o-methyl-d-ribofuranose → HCID 58681695, compound

HRID 30970Notes

Reaction equation

HRID 30970 reaction equation
C[C:2]1([O:22][C@H:21]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[C@@H:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[C@H:5]1[O:6]C(=O)C)[O:3][CH3:4]>C(=O)([O-])[O-].[K+].[K+]>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH2:12][O:11][C@@H:10]1[C@@H:21]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[O:22][CH:2]([O:3][CH3:4])[C@@H:5]1[OH:6]

Participants

3

Reactant 1

HCID 69037254Methyl-2-o-acetyl-3,5-bis-o-(2,4-dichlorobenzyl)-1-o-methyl-d-ribofuranose

Product 1

HCID 58681695HCID 58681695, compound

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

The compound prepared in Step 3 above (85.75 g, 0.1636 mol) in 820 mL of saturated methanolic potassium carbonate was stirred at ambient temperature for 45 minutes and then concentrated in vacuo. The oily residue was suspended in 820 mL of CH2Cl2, washed with water (493 mL+5×328 1 mL) and brine (328 mL), dried (NaSO4), filtered, and concentrated to give the product. The oil (75.93 g, 0.1573 mol) was immediatedly used in the next step without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with water (493 mL+5×328 1 mL) and brine (328 mL)
  3. dry with materialdried (NaSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the product

Sources & evidence

ORD record
ord-cd6ffc97f14b4307a0040d883dcf5530
Source dataset
uspto-grants-2008_09
Patent number
US07425547B2

Reaction notes

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