Water → HCID 86747342, Verbindung

HRID 1657202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657202
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86747342HCID 86747342, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
32 °C

Versuchsvorschrift

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].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-babfd9d012254510a06581084643bde6
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256800

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