UNCONVENTIONAL NUCLEOTIDE ANALOGUES .3. 4-(N1-PYRIMIDYL)-2-AMINOBUTYRIC ACIDS

被引:18
作者
NOLLET, AJH
PANDIT, UK
机构
[1] Laboratory of Oiganic Chemistry, University of Amsterdam, Amsterdam
关键词
D O I
10.1016/S0040-4020(01)83106-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkylation of 4-ethoxy-2-hydroxypyrimidines (10a, b), via their anions, provides a convenient procedure for preparing N1-substituted derivatives. Reaction of 10a, b with t-butyl 4-bromo-2-benzyloxycarbamidobutyrate (17) gives good yields of the N1-alkylated products 18a, b. The latter have been converted to uracil- (20a), thymine- (20b) and cytosine- (21) substituted α-aminobutyric acids. © 1969.
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页码:5989 / &
相关论文
共 22 条
[1]   NONCLASSICAL ANTIMETABOLITES .18. SIMULATION OF 5'-PHOSPHORIBOSYL BINDING .2. OMEGA-URACIL ALKANOIC ACIDS RELATED TO 2'-DEOXYURIDYLATE [J].
BAKER, BR ;
CHHEDA, GB .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1965, 54 (01) :25-&
[2]   SYNTHETIC SPECTROSCOPIC MODELS RELATED TO COENZYMES AND BASE PAIRS .2. EVIDENCE FOR INTRAMOLECULAR BASE-BASE INTERACTIONS IN DINUCLEOTIDE ANALOGS [J].
BROWNE, DT ;
ESINGER, J ;
LEONARD, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (26) :7302-&
[3]  
FOX JJ, 1959, ADV CARBOHYD CHEM, V14, P283
[4]   Researches on pyrimidines CXVII A method for the synthesis of nucleosides [J].
Hilbert, GE ;
Johnson, TB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1930, 52 :4489-4494
[5]   Action of alkali on 2,4-diethoxypyrimidine and the application of the reaction to a new synthesis of cytosine - The refractive indices of some pyrimidines [J].
Hilbert, GE ;
Jansen, EF ;
Hendricks, SB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1935, 57 (01) :552-554
[7]   ULTRAVIOLET SPECTRA OF N-HETEROCYCLIC SYSTEMS .1. THE ANIONS OF URACILS [J].
NAKANISHI, K ;
SUZUKI, N ;
YAMAZAKI, F .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1961, 34 (01) :53-57
[8]  
NISHIMURA T, 1965, CHEM PHARM B JAPAN, V13, P224
[9]   UNCONVENTIONAL NUCLEOTIDE ANALOGUES .2. SYNTHESIS OF ADENYL ANALOGUE OF WILLARDIINE [J].
NOLLET, AJH ;
PANDIT, UK .
TETRAHEDRON, 1969, 25 (24) :5983-&
[10]   UNCONVENTIONAL NUCLEOTIDE ANALOGUES .1. N9-PURINYL ALPHA-AMINO ACIDS [J].
NOLLET, AJH ;
HUTING, CM ;
PANDIT, UK .
TETRAHEDRON, 1969, 25 (24) :5971-&