Synthesis of (E)-5-[2-(tri-n-butylstannyl)vinyl] substituted 2′-deoxyuridine derivatives for use in halogenation and radiohalogenation reactions

被引：0
|
作者：
Yu, CS
Oberdorfer, F
机构：
[1] German Canc Res Ctr, Dept Radiopharmaceut Chem, D-69120 Heidelberg, Germany
[2] Univ Freiburg Klinikum, PET Zentrum, EUROPET GmbH, D-79106 Freiburg, Germany
来源：
SYNLETT | 2000年 / 01期
关键词：
terminal alkyne; stannylation; fluorodestannylation; radiohalogenation;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile synthesis is reported for 5-[2-(tri-n-butyl-stannyl)vinyl]-2'-deoxyuridine 1, starting from commercial 5-iodo-2'-deoxyuridine 2 via the stannylation reaction as the key step. The 3',5'-di-O-acetyl-N(3)-p-toluoyl-protected analog of 1, compound 9, was then prepared. Electrophilic fluorination of 9 with carrier-added [F-18]F-2 provided the desired (E) and (Z) fluorovinyl compounds 10, bur not as the major products. The E/Z ratio of 10 was 2:1. The main product of the reaction was the proton substituted compound 11.
引用
收藏
页码：86 / 88
页数：3
相关论文
共 50 条
  • [31] SYNTHESIS AND ANTIVIRAL PROPERTIES OF 5-(2-SUBSTITUTED VINYL)-6-AZA-2-'-DEOXYURIDINES
    MITCHELL, WL
    RAVENSCROFT, P
    HILL, ML
    KNUTSEN, LJS
    JUDKINS, BD
    NEWTON, RF
    SCOPES, DIC
    JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (05) : 809 - 816
  • [32] EFFICIENCY AND SELECTIVITY OF (E)-5-(2'-DEOXYURIDINE AND SOME OTHER 5-SUBSTITUTED 2'-DEOXYRIMIDINE NUCLEOSIDES AS ANTI-HERPES AGENTS
    REEFSCHLAGER, J
    BARWOLFF, D
    ENGELMANN, P
    LANGEN, P
    ROSENTHAL, HA
    ANTIVIRAL RESEARCH, 1982, 2 (1-2) : 41 - 52
  • [33] Nucleosides and nucleotides.: 170.: Synthesis and properties of oligodeoxynucleotides containing 5-[N-[2-[N,N-bis(2-aminoethyl)amino]ethyl]carbamoyl]-2′-deoxyuridine and 5-[N-[3-[N,N-bis(3-aminopropyl)amino]propyl]carbamoyl]-2′-deoxyuridine
    Ueno, Y
    Mikawa, M
    Matsuda, A
    BIOCONJUGATE CHEMISTRY, 1998, 9 (01) : 33 - 39
  • [34] Nucleosides and nucleotides. 170. Synthesis and properties of oligodeoxynucleotides containing 5-[N-[2-[N,N-bis(2-aminoethyl)-amino]ethyl]carbamoyl]-2'-deoxyuridine and 5-[N-[3-[N,N bis(3-aminopropyl)amino]propyl]carbamoyl]-2'-deoxyuridine
    Ueno, Yoshihito
    Mikawa, Mai
    Matsuda, Akira
    Bioconjugate Chemistry, 9 (01): : 33 - 39
  • [35] FORMATION OF TIN-NITROGEN BONDS .5. SELECTIVE 1-SUBSTITUTION REACTION OF TETRAZOLES BY REACTION OF 5-SUBSTITUTED 2-(TRI-N-BUTYLSTANNYL)TETRAZOLES WITH METHYL-IODIDE, METHYL PARA-TOLUENESULFONATE, DIMETHYL SULFATE, AND ETHYL BROMOACETATE
    ISIDA, T
    AKIYAMA, T
    NABIKA, K
    SISIDO, K
    KOZIMA, S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (07) : 2176 - 2180
  • [36] Efficient synthesis of n-oxide derivatives:: Substituted 2-(2-(Pyridyl-N-oxide) methylsulphinyl) benzimidazoles
    Ray, Purna C.
    Mittapelli, Vasantha
    Rohatgi, Amit
    Tyagi, Om Dutt
    SYNTHETIC COMMUNICATIONS, 2007, 37 (17) : 2861 - 2868
  • [37] Synthesis of 2-[5-(substituted phenyloxy)methyl-1,3,4-thiadiazol-2-ylimino]-5-(substituted benzylidene)-4-thiazolidinones
    Wang, Xi-Cun
    Huang, Guo-Li
    Quan, Zheng-Jun
    Lue, Cheng-Wei
    Yang, Wen-Long
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (05) : 870 - 874
  • [38] STUDIES ON NITROFURAN DERIVATIVES .4. SYNTHESIS OF 2- OR 4-[2-(5-NITRO-2-FURYL)VINYL]PYRIMIDINE DERIVATIVES
    FUJITA, A
    YAMAMOTO, T
    MINAMI, S
    TAKAMATSU, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1965, 13 (10) : 1183 - +
  • [39] Synthesis and biological evaluation of (E)-cinnamic acid, (E)-2-styrylthiazole and (E)-2-[2-(naphthalen-1-yl)vinyl]thiazole derivatives
    Olawode, Emmanuel O.
    Tandlich, Roman
    Prinsloo, Earl
    Isaacs, Michelle
    Hoppe, Heinrich
    Seldon, Ronnett
    Warner, Digby F.
    Steenkamp, Vanessa
    Kaye, Perry T.
    ARKIVOC, 2016, : 284 - 296
  • [40] PROBLEMS ASSOCIATED WITH THE USE OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE FOR TYPING HERPES-SIMPLEX VIRUS
    SWIERKOSZ, EM
    ARENS, MQ
    RIVETNA, KA
    JOURNAL OF CLINICAL MICROBIOLOGY, 1985, 21 (03) : 459 - 461
12345