Water → HCID 19096634, compound

HRID 486843Notes

Reaction equation

C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.O.[CH3:25][C:26]1([CH3:40])[O:31][C:30](=[O:32])[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][C:30](=[O:32])[CH:29]=[C:28]([CH2:33][CH:34]([OH:39])[CH2:35][N:36]=[N+:37]=[N-:38])[O:27]1

Participants

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-4-one [a compound having the formula (1) in which n is 1, X is N3, Y is a hydrogen atom, and a substituent is present at the 6-position].

Workup

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

Sources & evidence

ORD record: ord-2152514220d347afb33095f180608d7e
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292891

Reaction notes

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