HCID 68837944, compound → HCID 11173988, compound
Reaction equation
P([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[CH:17][C:15](=[O:16])[NH:14][C:12]2=[O:13])[C@H:8]([O:19][CH2:20][CH2:21][C:22]#[N:23])[C@@H:7]1[OH:24])(N)O>C(#N)C>[C:22]([CH2:21][CH2:20][O:19][C@@H:8]1[C@H:7]([OH:24])[C@@H:6]([CH2:5][OH:4])[O:10][C@H:9]1[N:11]1[CH:18]=[CH:17][C:15](=[O:16])[NH:14][C:12]1=[O:13])#[N:23]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
RNA synthesis program (condensation time: 10 min.) was carried out using four kinds of anhydrous acetonitrile solution of 2′-O-cyanoethyluridine phosphoramidite unit (compounds 7, 14, 18 and 26, 0.1M) by means of a DNA/RNA automatic synthesizer (Applied Bio System) provided with a long aminoalkyl chain CPG (1 μl) in which 2′-O-cyanoethyluridine was introduced via a succinyl linker by a conventional way (16 μl mol/g), which was filled into a socket for solid-phase synthesis. After the synthesis had been completed, excision of the resulting oligonucleotide from the solid phase and removal of a protecting group of the nucleic acid base moiety were carried out by treatment with ammonia water-ammonium acetate (10% wt/wt: 1 ml) for 90 min. After diluted appropriately with ammonium acetate buffer, the oligonucleotides were purified with a reverse phase column cartridge and an anion exchange HPLC. The oligonucleotides obtained by a desalting operation with the reverse phase column cartridge were lyophilized to give a titled compound with a yield of 58%. Analysis profile obtained in the anion exchange HPLC is shown in FIG. 1B.
Sources & evidence
- ORD record
- ord-a8dd86b1e7bb47c6a74f840400c2048b
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07569685B2
Reaction notes
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