Sucrose → ethyl (2R,3S)-2-ethyl-3-hydroxybutyrate

HRID 355641

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HRID 355641 반응식
C(O)[C@H]1O[C@H:6]([O:8][C@:9]2(CO)[O:13][C@H:12](CO)[C@@H:11]([OH:16])[C@@H:10]2O)[C@H:5](O)[C@@H](O)[C@@H]1O.[CH3:24][C@H:25]([C@@H](O)C)C(OCC)=O.C[C@@H]([C@@H](O)C)C(OCC)=O>O.C(O)C.S(=O)(=O)(O)O.OP(O)=O.O[Mo](O)(=O)=O>[CH2:24]([C@H:10]([C@@H:11]([OH:16])[CH3:12])[C:9]([O:8][CH2:6][CH3:5])=[O:13])[CH3:25]

참가 물질

8

반응물 3

HCID 5988SucroseHCID 642623ethyl-(2R)-methyl-(3S)-hydroxybutanoateHCID 11789342ethyl (2S,3S)-3-hydroxy-2-methylbutanoate

생성물 1

HCID 13215285ethyl (2R,3S)-2-ethyl-3-hydroxybutyrate

시약·촉매·용매 4

HCID 21863154Dihydroxy(dioxo)molybdenum;phosphonic acid촉매HCID 702Ethanol용매HCID 962Water용매HCID 1118Sulfuric Acid용매

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온도
30 °C

실험 절차

Twenty grams of bakers' yeast (Sigma Chemical Company, Saccharomyces cerevisiae, type II) was suspended in a solution of 30 grams of sucrose in water in a conical flask, and the mixture was placed in an orbital shaker chamber maintained at 220 rpm and 30° C. for 30 minutes to initiate fermentation. Two grams of ethyl 2-ethyl acetoacetate was dissolved in 2 ml of 95% ethanol, the resulting solution was added to the fermenting yeast, and shaking was resumed. The reaction was followed by TLC (staining with phosphomolybdic acid in ethanolic sulfuric acid) to monitor the consumption of starting material and the production of product alcohol. After approximately 48 hours the reaction was judged complete, and the reaction was terminated by removing the flask from the shaker and adding 20-30 grams of Celite to the reaction mixture. The resulting suspension was suction filtered through a pad of Celite, and the clear yellow filtrate was extracted with ethyl acetate (4×200 ml). The extracts were combined, dried over MgSO4, filtered, and rotary evaporated to leave 1.6 grams of a yellowish oil containing ethyl (2R,3S)-2-methyl-3-hydroxybutyrate as the major product (80%) and ethyl (2S,3S)-2-methyl-3-hydroxybutyrate (20%) as the minor product as judged by chiral chromatography.

후처리

  1. additionthe resulting solution was added to the fermenting yeast
  2. customthe consumption of starting material
  3. customthe reaction was terminated
  4. customby removing the flask from the shaker
  5. additionadding 20-30 grams of Celite to the reaction mixture
  6. filtrationfiltered through a pad of Celite
  7. extractionthe clear yellow filtrate was extracted with ethyl acetate (4×200 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customrotary evaporated
  11. customto leave 1.6 grams of a yellowish oil

출처 및 근거

ORD 기록
ord-cac7673be92c4346afdbea1336040fb1
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834261

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