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

HRID 619691노트

반응식

HRID 619691 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 1508512'Fluoro-2'-deoxyuridine수율 75%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

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출처 및 근거

ORD 기록
ord-bd9d0cdd69934663ac887ad8626483ca
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05959096

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