L-Fucal → 1,5-anhydro-3-oxo-2,3,6-trideoxy-L-threo-hex-1-enitol

HRID 1155326Notes

Reaction equation

HRID 1155326 reaction equation
[CH3:1][C@@H:2]1[O:7][CH:6]=[CH:5][C@H:4]([OH:8])[C@@H:3]1[OH:9]>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2].C([O-])([O-])=O.[Ag+].[Ag+]>[O:8]=[C:4]1[C@H:3]([OH:9])[C@H:2]([CH3:1])[O:7][CH:6]=[CH:5]1

Participants

5

Reactant 1

HCID 11083911L-Fucal

Product 1

HCID 128167791,5-anhydro-3-oxo-2,3,6-trideoxy-L-threo-hex-1-enitol

Reagents, catalysts & solvents 3

HCID 92796Silver carbonateCatalystHCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolvent

Procedure

In a 250 milliliter round-bottomed flask, 1 gram of L-fucal [Example 5 product] is dissolved in 100 milliliters of benzene. To this solution was added 20-25 grams of silver carbonate on celite (Fetizon's reagent), prepared as described below, and the mixture was stirred. The flask was equipped for simple distillation, and 20-25 milliliters of solvent was removed by distillation. During this time the yellow Fetizon's reagent becomes dark brown. The distillation assembly is replaced with an efficient reflux condenser and the mixture is refluxed for 1 hour, after which time the reaction is generally completed as judged by t.l.c. monitoring. The hot mixture is filtered through celite and the filtrate evaporated under reduced pressure to give 1,5-anhydro-3-oxo-2,3,6-trideoxy-L-threo-hex-1-enitol.

Workup

  1. customprepared
  2. customwas removed by distillation
  3. distillationThe distillation
  4. customassembly is replaced with an efficient reflux condenser
  5. temperaturethe mixture is refluxed for 1 hour
  6. filtrationThe hot mixture is filtered through celite
  7. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-166bebeb578e4543948968928c145247
Source dataset
uspto-grants-1981_11
Patent number
US04301276

Reaction notes

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