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

HRID 2372145ノート

反応式

HRID 2372145 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0eb5f4b01683457591f7aefafea005cd
出典データセット
uspto-grants-1992_03
特許番号
US05097023

反応ノート

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