Hydrochloric Acid → 1,5-Anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-xylo-hexitol
反応式
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].O1CCCC1.[N:20]([C@H:23]1[CH2:37][O:36][C@H:26]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[C:25](=[O:38])[CH2:24]1)=[N+:21]=[N-:22].Cl>O1CCCC1>[N:20]([C@@H:23]1[CH2:24][C@@H:25]([OH:38])[C@@H:26]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[O:36][CH2:37]1)=[N+:21]=[N-:22]参加物
5
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -78 °C
実験手順
Lithium tri-sec-butylborohydride/tetrahydrofuran solution (1.0 mol/l, 0.83 ml, 0.83 mmol) was added to a tetrahydrofuran (2.5 ml) solution of the compound (169 mg, 0.59 mmol) obtained in Step 1 above at −78° C. and the resulting mixture was stirred at −78° C. for 45 minutes. 1N hydrochloric acid was added, the resulting mixture was subjected to extraction with ethyl acetate and the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=20:1→12:1 (v/v)] to give 101 mg (59%) of the title compound as a colorless oil.
後処理
- extractionthe resulting mixture was subjected to extraction with ethyl acetate
- washthe organic layer was washed with brine
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=20:1→12:1 (v/v)]
出典と根拠
- ORDレコード
- ord-4ac0f7ff711e43ebb6e19be1cd291fe5
- 出典データセット
- uspto-grants-2014_01
- 特許番号
- US08629133B2
反応ノート
読み込み中…