Water → HCID 86747342, compound

HRID 1657202Notes

Reaction equation

HRID 1657202 reaction equation
C(O)[C@H]1O[C@H]([O:8][C@:9]2(CO)[O:13][C@H:12](CO)[C@@H:11](O)[C@@H:10]2[OH:17])[C@H](O)[C@@H](O)[C@@H]1O.O.[CH3:25][C:26]1([CH3:40])[O:31][C:30](=O)[CH:29]=[C:28]([CH2:33][C:34](=[O:39])[CH2:35][N:36]=[N+:37]=[N-:38])[O:27]1>C(OCC)(=O)C>[CH3:25][C:26]1([CH3:40])[O:31][CH2:30][CH:29]=[C:28]([CH2:33][CH:34]([OH:39])[CH2:35][N:36]=[N+:37]=[N-:38])[O:27]1.[O:13]1[CH:12]=[CH:11][C:10](=[O:17])[O:8][CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 5988Sucrose2×HCID 19096639HCID 19096639, compound

Product 1

HCID 86747342HCID 86747342, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
32 °C

Procedure

30 g of baker's yeast (made by Oriental Yeast Co., Ltd.) and 15 g of saccharose were added in 30 ml of tap water, and the solution was then stirred at 32° C. for 30 minutes. Afterward, 300 mg of 2,2-dimethyl-6-(3-azido-2-oxopropyl)-1,3-dioxin-4-one were added thereto, and the solution was then stirred overnight at the same temperature. 7.5 g of saccharose were further added thereto, followed by stirring overnight. Water of the reaction solution was then distilled off under reduced pressure, and the residue was extracted with dichloromethane and then dried over anhydrous sodium sulfate. Afterward, the solvent was distilled off, and the resultant residue was then subjected to column chromatography (an eluent of hexane:ethyl acetate=4:1), thereby obtaining 67 mg (yield 22%) of (+)-2,2-dimethyl-6-(3-azido-2-hydroxypropyl)-1,3-dioxin-1,3-dioxin-4-one [a compound having the formula (1) in which n is 1, X is N3, Y is a hydrogen atom, and the substituent is present at the 6-position].

Workup

  1. stirringthe solution was then stirred overnight at the same temperature
  2. stirringby stirring overnight
  3. distillationWater of the reaction solution was then distilled off under reduced pressure
  4. extractionthe residue was extracted with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfterward, the solvent was distilled off

Sources & evidence

ORD record
ord-babfd9d012254510a06581084643bde6
Source dataset
uspto-grants-1993_10
Patent number
US05256800

Reaction notes

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