反応 #453124

ord-b44a2c40fc0b41dca52d89218a785ec8

反応方程式

Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O
compound 105
Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O
5'--O-tert-Butyldiphenylsilyl-2'--O-[N,N-dimethylaminooxyethyl]-5-methyluridine
CCN(CC)CC.F.F.F
Triethylamine trihydrofluoride
CCN(CC)CC
triethylamine
CO
MeOH
Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O
106
収率 92.5%
Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O
2'--O-(dimethylaminooxyethyl)-5-methyluridine
収率 92.5%

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他Reaction
  2. 2
    その他Solvent removed under vacuum
  3. 3
    洗浄eluted with 10% MeOH in CH2Cl9

実験手順

Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to compound 105 (1.40 g, 2.4 mmol) and stirred at room temperature for 24 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Solvent removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl9 to get 106 (766 mg, 92.5%). Rf 0.27 (5% MeOH in CH2Cl2). MS (FAB⊕) m/e 346 (M+H⊕)

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US06127533uspto-grants-2000_10