反应 #927232

ord-82719d70619f450788653d52902c639d

反应方程式

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
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
2′-O-(dimethylaminooxyethyl)-5-methyluridine
收率 92.5%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他Reaction
  2. 2
    其他Solvent was removed under vacuum
  3. 3
    洗涤eluted with 10% MeOH in CH2Cl2

实验过程

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 5′-O-tert-butyldiphenylsilyl-2′-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for 24 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Solvent was removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get 2′-O-(dimethylaminooxyethyl)-5-methyluridine (766 mg, 92.5%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US06365354B1uspto-grants-2002_04