تفاعل #1951042

ord-e08bc9c0df6740278e77a2f91a0db294

معادلة التفاعل

CCCC[N+](CCCC)(CCCC)CCCC.[F-]
tetrabutylammonium fluoride
CC(=O)O
acetic acid
CC[Si](C#C[C@@]1(CO[Si](C)(C)C(C)(C)C)CC[C@H](n2cnc3c(N)nc(F)nc32)O1)(CC)CC
Compound 22
CC[Si](C#C[C@@]1(CO[Si](C)(C)C(C)(C)C)CC[C@H](n2cnc3c(N)nc(F)nc32)O1)(CC)CC
5′-O-t-butyldimethylsilyl-2′,3′-dideoxy-4′-C-triethylsilylethynyl-2-fluoroadenosine
C#C[C@@]1(CO)CC[C@H](n2cnc3c(N)nc(F)nc32)O1
2′,3′-dideoxy-4′-C-ethynyl-2-fluoroadenosine

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىreaction mixture
  2. 2
    تركيزthe resultant mixture was concentrated under reduced pressure
  3. 3
    أخرىThe thus-obtained residue was purified by means of silica gel column chromatography (silica gel 15 ml, chloroform:methanol=40:1 to 20:1)

الإجراء التجريبي

Compound 22 (101 mg, 0.200 mmol) was dissolved in tetrahydrofuran (10 ml), and a solution of 1-M tetrabutylammonium fluoride in tetrahydrofuran (0.42 ml, 0.42 mmol) was added to the resultant solution, followed by stirring at room temperature for five minutes. After acetic acid (24 μl) was added to the resultant reaction mixture, the resultant mixture was concentrated under reduced pressure. The thus-obtained residue was purified by means of silica gel column chromatography (silica gel 15 ml, chloroform:methanol=40:1 to 20:1), to thereby yield compound 23 (53.0 mg, 0.191 mmol, 95.7%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07625877B2uspto-grants-2009_12