Convenient syntheses of 6-methylpurine and related nucleosides

被引:22
作者
Hassan, AEA [1 ]
Abou-Elkair, RAI [1 ]
Montgomery, JA [1 ]
Secrist, JA [1 ]
机构
[1] So Res Inst, Dept Organ Chem, Drug Discovery Div, Birmingham, AL 35255 USA
关键词
D O I
10.1080/15257770008035035
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Efficient methods for the synthesis of 6-methylpurine (3), 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-6-methylpurine (8), and 6-methyl-9-beta-D-ribofuranosylpurine (5) are described. Methodology involving the (Ph3P)(4)Pd catalyzed cross-coupling reaction of CH3ZnBr with several different 6-chloropurine derivatives is described in high yield. This methodology now provides a facile and high-yielding synthesis of 8, which is needed in significant amounts for studies in cancer gene therapy.
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收藏
页码:1123 / 1134
页数:12
相关论文
共 32 条
[1]   Stereoselective synthesis of 6-methyl-9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine [J].
AndersonMcKay, JE ;
Both, GW ;
Simpson, GW .
NUCLEOSIDES & NUCLEOTIDES, 1996, 15 (7-8) :1307-1313
[2]   TRIS(TRIMETHYLSILYL)SILANE AND DIPHENYLSILANE IN THE RADICAL CHAIN DIDEOXYGENATION OF 1,6-ANHYDRO-D-GLUCOSE - A COMPARATIVE-STUDY [J].
BARTON, DHR ;
JANG, DO ;
JASZBERENYI, JC .
TETRAHEDRON LETTERS, 1992, 33 (44) :6629-6632
[3]   RADICAL MONODEOXYGENATION AND DIDEOXYGENATION WITH THE TRIETHYLSILANE + BENZOYL PEROXIDE SYSTEM [J].
BARTON, DHR ;
JANG, DO ;
JASZBERENYI, JC .
TETRAHEDRON LETTERS, 1991, 32 (49) :7187-7190
[4]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[5]   ACTIVITY OF ADENOSINE ANALOGS AGAINST A CELL CULTURE LINE RESISTANT TO 2-FLUOROADENINE [J].
BENNETT, LL ;
VAIL, MH ;
CHUMLEY, S ;
MONTGOMERY, JA .
BIOCHEMICAL PHARMACOLOGY, 1966, 15 (11) :1719-+
[6]   A novel approach to synthesis of 2′-deoxy-β-D-ribonucleosides via transglycosylation of 6-oxopurine ribonucleosides [J].
Boryski, J .
NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (9-11) :1547-1556
[7]   AN UNAMBIGUOUS SYNTHESIS OF ADENYLOSUCCINIC ACID AND ITS CONSTITUENT NUCLEOSIDE [J].
BUCK, IM ;
REESE, CB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :2937-2942
[8]  
CLARKE D A, 1954, Ann N Y Acad Sci, V60, P235
[9]  
Dvorakova H, 1996, TETRAHEDRON LETT, V37, P1285
[10]   A POTENTIAL TRANSITION STATE ANALOG FOR ADENOSINE DEAMINASE [J].
EVANS, B ;
WOLFENDEN, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (15) :4751-+