Pyridine, hydrofluoride (1:1) → 2'Fluoro-2'-deoxyuridine

HRID 619691ノート

反応式

HRID 619691 の反応式
[CH:1]1[C:15](=[O:16])[N:14]=[C:13]2[N:3]([C@@H:4]3[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]3[O:12]2)[CH:2]=1.C1C=CN=CC=1.[FH:23]>O1CCOCC1>[F:23][C@@H:5]1[C@H:6]([OH:11])[C@@H:7]([CH2:9][OH:10])[O:8][C@H:4]1[N:3]1[CH:2]=[CH:1][C:15](=[O:16])[NH:14][C:13]1=[O:12]

参加物

4

反応物 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 8061382,2'-Anhydrouridine

生成物 1

HCID 1508512'Fluoro-2'-deoxyuridine収率 75%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

2,2'-Cyclouridine is treated with a solution of 70% hydrogen fluoride/pyridine in dioxane at 120° C. for ten hours to provide after solvent removal a 75% yield of 2'-deoxy-2'- fluorouridine. The 5'-DMT and 3'-cyanoethoxydiisopropylphos-phoramidite derivitized nucleoside is obtained by standard literature procedures, M. J. Gait, ed., Oligonucleotide Synthesis. A Practical Approach, (IRL Press, Washington, D.C., 1984) or through the procedure of Example 25A.

後処理

  1. customto provide

出典と根拠

ORDレコード
ord-bd9d0cdd69934663ac887ad8626483ca
出典データセット
uspto-grants-1999_09
特許番号
US05959096

反応ノート

読み込み中…