Reaction #466003

ord-695481754f0e4062802b6e1befa4d4a9

Reaction equation

CC(=O)OC[C@H]1O[C@@H](n2cc(C#C[Si](C)(C)C)c(=O)[nH]c2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
product
CC(=O)OC[C@H]1O[C@@H](n2cc(C#C[Si](C)(C)C)c(=O)[nH]c2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
2′,3′,5′-Tri-O-Acetyl-5-[2-(trimethylsilyl)ethynyl]uridine
[Na]
sodium
→
C#Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O
beige solid
C#Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O
5-Ethynyluridine

Reactants

CC(=O)OC[C@H]1O[C@@H](n2cc(C#C[Si](C)(C)C)c(=O)[nH]c2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
product
CC(=O)OC[C@H]1O[C@@H](n2cc(C#C[Si](C)(C)C)c(=O)[nH]c2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
2′,3′,5′-Tri-O-Acetyl-5-[2-(trimethylsilyl)ethynyl]uridine
[Na]
sodium

Reagents

None

Solvents

CO
methanol
CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONdiluted with a solution
  2. 2
    OtherThe resin was removed
  3. 3
    Filtrationby filtering
  4. 4
    Washwashed with methanol
  5. 5
    ConcentrationThe filtrate was concentrated in vacuo

Procedure

The product of stage b) (9.5 g, 24 mmol) was dissolved in methanol (200 mL) and diluted with a solution containing sodium (0.8 g) and methanol (100 mL). The reaction was stirred at room temperature for 2 hours and was then neutralized using Dowex 50W-X8 (H+ form) resin. The resin was removed by filtering and washed with methanol. The filtrate was concentrated in vacuo to give 4.85 g of a beige solid. The compound was purified on a Waters Prep 500 reverse phase C18 column which was eluted with H2O/MeOH 85:15 (v:v) to give 1.2 g of the title product (white solid). Impure fractions were re-chromatographed. An additional 1.94 g of product were obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06297223B1uspto-grants-2001_10