Trifluoroacetic acid → Methyl 2,3,5-tri-O-benzyl-L-xylofuranose

HRID 2372145노트

반응식

HRID 2372145 반응식
[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:13][CH:10]1[O:11]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:34](F)(F)C(O)=O>O.C(OCC)(=O)C>[CH3:34][C:10]1([O:13][C@@H:14]([CH2:24][O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:9]1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:11]

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 11015596methyl 2,3,5-tri-O-benzyl-L-xylofuranoside

생성물 1

HCID 131717204Methyl 2,3,5-tri-O-benzyl-L-xylofuranose수율 53%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

Methyl 2,3,5-tri-O-benzyl-L-xylofuranoside (22.7 g, 56.30 mmol) is dissolved at 0° C. in a 9:1 mixture of trifluoroacetic acid and water (200 mL) and stirred at 0° C. overnight. The mixture is put to dryness under reduced pressure. The oily residue is dissolved in ethyl acetate and washed three times with a saturated solution of sodium bicarbonate. The organic layer is dried over sodium sulfate, filtered and put to dryness under reduced pressure to afford an oil. Flash chromatography on silica gel and elution with a 7:3 mixture of cyclohexane and ethyl acetate yield methyl 2,3,5-tri-O-benzyl-L-xylofuranose as an oil (11.7 g, 53%).

후처리

  1. washwashed three times with a saturated solution of sodium bicarbonate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. customto afford an oil
  5. washFlash chromatography on silica gel and elution
  6. additionwith a 7:3 mixture of cyclohexane and ethyl acetate

출처 및 근거

ORD 기록
ord-0eb5f4b01683457591f7aefafea005cd
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05097023

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