Hydrochloric Acid → (1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-Dioxabicyclo [3.2.1]Octane

HRID 6786Notes

Reaction equation

HRID 6786 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:13]([C@@H:14]([CH2:23][O:24]S(C2C=CC(C)=CC=2)(=O)=O)[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:12][C@@H:11]([N:35]2[CH:43]=[C:41]([CH3:42])[C:39](=[O:40])[NH:38][C:36]2=[O:37])[C@@H:10]1OS(C1C=CC(C)=CC=1)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C.O>[CH2:16]([O:15][C@H:14]1[C@@H:13]2[C@@H:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@H:10]([C@H:11]([N:35]3[CH:43]=[C:41]([CH3:42])[C:39](=[O:40])[NH:38][C:36]3=[O:37])[O:12]2)[O:24][CH2:23]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 107715111-(3,5-Di-o-benzyl-2,6-di-o-(p-toluenesulphonyl)-beta-d-allofuranosyl)thymine

Product 1

HCID 57198644(1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-Dioxabicyclo [3.2.1]Octane

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of nucleoside 17 (0.63 g, 0.81 mmol) in a mixture of ethanol and H2O (40 cm3, 1:1, v/v) at room temperature was added an aqueous solution of sodium hydroxide (1M, 7 cm3). The resulting mixture was heated under reflux for 16 h and then neutralised by addition of dilute hydrochloric acid (10 cm3). The volume of the mixture was reduced to 50% and extraction was performed using dichloromethane (50 cm3×3). The combined organic phase was dried (Na 2SO4) and evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (99:1,v/v) as eluent to give nucleoside 18 as a white solid material (0.40 g, 93%) after evaporation of the solvents under reduced pressure.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 16 h
  3. extractionThe volume of the mixture was reduced to 50% and extraction
  4. dry with materialThe combined organic phase was dried (Na 2SO4)
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ecd940dc36e2454898ef625089e089bf
Source dataset
uspto-grants-2006_08
Patent number
US07084125B2

Reaction notes

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