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Trifluoromethanesulfonic anhydride → Methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranoside

HRID 1531577
ノート
印刷プレビュー

反応式

HRID 1531577 の反応式
[Si](O[CH2:19][C@H:20]1[O:27][C@@H:24]([O:25][CH3:26])[C@H:23]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:22]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:21]1[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.[S:67]([O:74]S(C(F)(F)F)(=O)=O)([C:70]([F:73])([F:72])[F:71])(=[O:69])=[O:68]>ClCCl>[CH2:29]([O:28][C@@H:23]1[C@@H:22]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C@H:21]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@@H:20]([CH2:19][O:74][S:67]([C:70]([F:73])([F:72])[F:71])(=[O:69])=[O:68])[O:27][C@H:24]1[O:25][CH3:26])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 11146901Methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-beta-D-glucopyranoside

生成物 1

HCID 22842886Methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranoside

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside (800 mg, 1.71 mmol) in 8.55 mL of dry dichloromethane at −78° C. was added 2,6-di-tert-butyl-4-methyl pyridine (632 mg, 3.08 mmol) followed by triflic anhydride (345 μl, 2.05 mmol). After stirring 15 minutes at −78° C., the mixture was warmed to room temperature over 20 minutes, and then poured into a solution of saturated aqueous NaHCO, (20 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with saturated NaHCO3 (3×20 mL), saturated aqueous NaCl (1×20 mL), and dried over magnesium sulfate. Concentration provided crude target compound, which was used in the next step without further purification.

後処理

  1. temperaturethe mixture was warmed to room temperature over 20 minutes
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with saturated NaHCO3 (3×20 mL), saturated aqueous NaCl (1×20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentration
  6. customprovided crude target compound, which
  7. customwas used in the next step without further purification

出典と根拠

ORDレコード
ord-348a8dadc00c41e2a339e929ba65989d
出典データセット
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06197963B1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート