Efficient removal of sugar O-tosyl groups and heterocycle halogens from purine nucleosides with sodium naphthalenide

被引:7
作者
Lewandowska, E [1 ]
Neschadimenko, V [1 ]
Wnuk, SF [1 ]
Robins, MJ [1 ]
机构
[1] BRIGHAM YOUNG UNIV,DEPT CHEM & BIOCHEM,PROVO,UT 84602
关键词
D O I
10.1016/S0040-4020(97)00313-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sodium naphthalenide effects removal of 2'-, 3'-, or 5'-O-tosyl groups from the sugar, and 2-, 6-, or 8-halogens from purine nucleosides. An improved tosyl protection strategy was developed for the synthesis of 9-(3-deoxy-3-fluoro-beta-D-xylofuranosyl)adenine from 2',5'-di-O-tosyladenosine. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:6295 / 6302
页数:8
相关论文
共 28 条
[1]   A FACILE PREPARATION OF AROMATIC ANION RADICALS BY ULTRASOUND IRRADIATION [J].
AZUMA, T ;
YANAGIDA, S ;
SAKURAI, H ;
SASA, S ;
YOSHINO, K .
SYNTHETIC COMMUNICATIONS, 1982, 12 (02) :137-140
[2]   THE CHEMISTRY OF 2', 3'-SECONUCLEOSIDES .3. SYNTHESIS AND REACTIONS OF PURINE-2', 3'-SECORIBONUCLEOSIDES [J].
BEATON, G ;
JONES, AS ;
WALKER, RT .
TETRAHEDRON, 1988, 44 (20) :6419-6428
[3]   REDUCTIVE CLEAVAGE OF TOLUENESULFONATES WITH SODIUM NAPHTHALENE [J].
CLOSSON, WD ;
WRIEDE, P ;
BANK, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (07) :1581-&
[4]  
CLOSSON WD, 1982, J ORG CHEM, V47, P276
[5]  
DAVID S, 1972, B SOC CHIM FR, P3610
[6]  
EBEL HF, 1970, HOUBEN WEYL, V13, P255
[7]   ELECTRON TRANSFER, NAPHTHALENE RADICAL ANION, AND ALKYL HALIDES [J].
GARST, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (12) :400-&
[8]   PURINE NUCLEOSIDES .4. SYNTHESIS OF 6-HALOGENATED 9-BETA-D-RIBOFURANOSYLPURINES FROM INOSINE AND GUANOSINE [J].
GERSTER, JF ;
ROBINS, RK ;
JONES, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (04) :945-&
[9]  
GREENE GL, 1975, TETRAHEDRON LETT, P2081
[10]   REACTION OF ADENINE NUCLEOSIDES, TOSYLATED IN THE CARBOHYDRATE MOIETY, WITH LITHIUM TRIETHYLBOROHYDRIDE [J].
HERDEWIJN, P .
TETRAHEDRON, 1989, 45 (20) :6563-6580