Dichloromethane → 1,5-Anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-ribo-hexitol

HRID 470702ノート

反応式

HRID 470702 の反応式
ClCCl.[C:4]([Si:8]([CH3:11])([CH3:10])Cl)([CH3:7])([CH3:6])[CH3:5].[N:12]([C@@H:15]1[CH2:20][C@H:19]([OH:21])[C@@H:18]([CH2:22][OH:23])[O:17][CH2:16]1)=[N+:13]=[N-:14].C(N(CC)CC)C>C(Cl)(Cl)Cl>[N:12]([C@@H:15]1[CH2:20][C@H:19]([OH:21])[C@@H:18]([CH2:22][O:23][Si:8]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:11])[CH3:10])[O:17][CH2:16]1)=[N+:13]=[N-:14]

参加物

6

反応物 4

HCID 6344Dichloromethane2 回HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 866726091,5-Anhydro-2-azido-2,3-dideoxy-D-glucitol

生成物 1

HCID 866726081,5-Anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-ribo-hexitol収率 89%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A dichloromethane (4 ml) solution of tert-butyldimethylchlorosilane (381 mg, 2.54 mmol) was added to a dichloromethane (10 ml) solution of 1,5-anhydro-2-azido-2,3-dideoxy-D-ribo-hexitol (440 mg, 2.54 mmol) and triethylamine (0.46 ml, 3.30 mmol) under ice cooling. After stirring at room temperature for 50 hours, the reaction mixture was diluted with chloroform and the organic layer was washed with water and 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=10:1→4:1 (v/v)] to give 650 mg (89%) of the title compound as a colorless oil.

後処理

  1. washthe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=10:1→4:1 (v/v)]

出典と根拠

ORDレコード
ord-fd155648853541b3aec9b0c2bda80fd3
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…